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Publication numberUS3993682 A
Publication typeGrant
Application numberUS 05/572,224
Publication date23 Nov 1976
Filing date28 Apr 1975
Priority date15 May 1974
Also published asCA1071649A1, DE2423679A1, DE2423679B2
Publication number05572224, 572224, US 3993682 A, US 3993682A, US-A-3993682, US3993682 A, US3993682A
InventorsHeinrich Kolling, Herbert Thomas, Arno Widdig, Hartmund Wollweber
Original AssigneeBayer Aktiengesellschaft
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Substituted phenylguanidines and processes for their preparation and use
US 3993682 A
Abstract
N-[2-(Substituted amido)phenyl]-N',N"-bis-carbonylguanidines bearing an optionally substituted phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl group in the 4- or 5-position of the 2-(substituted amido)phenyl group are anthelmintic agents. The compounds, of which N-(2-acetamido-4-phenylthiophenyl)-N',N"-bis-carbomethoxyguanidine is a typical example, are prepared through the reaction of isothiourea-S-alkyl ether and an appropriately substituted 2-aminoanilide.
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Claims(11)
What is claimed is:
1. A member selected from the group consisting of an N-(4-phenylthio-2-amidophenyl)guanidine compound of the formula: ##SPC23## ##SPC24##
and an N-(5-phenylthio-2-amidophenyl)guanidine of the formula: ##SPC25##
wherein
R4 is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkoxy of 1 to 6 carbon atoms, phenyl, phenylalkyl of 7 to 12 carbon atoms, alkoxyalkyl of 2 to 12 carbon atoms, phenoxyalkyl of 7 to 12 carbon atoms, amino, alkylamino of 1 to 6 carbon atoms or dialkylamino wherein each alkyl group contains 1 to 6 carbon atoms;
R5 is alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms or alkynyl of 2 to 6 carbon atoms; and
R6 is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, phenyl, phenylalkyl of 7 to 12 carbon atoms, phenoxyalkyl of 7 to 12 carbon atoms, alkoxyalkyl of 2 to 12 carbon atoms or alkoxyalkoxy of 2 to 12 carbon atoms;
each of R2 and R3 independent of the other is hydrogen, halogeno, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, trifluoromethyl, alkanoyl of 1 to 6 carbon atoms, amino, alkanoylamino of 1 to 6 carbon atoms or carbalkoxy of 2 to 7 carbon atoms.
2. A compound according to claim 1 in which ##SPC26##
R4 is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms, phenyl, benzyl or phenethyl;
R5 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, or alkynyl of 2 to 4 carbon atoms;
R6 is hydrogen, alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, alkenyloxy of 2 to 4 carbon atoms, alkynyloxy of 2 to 4 carbon atoms, alkoxyalkyl of 2 to 8 carbon atoms, alkoxyalkoxy of 2 to 8 carbon atoms, phenyl, benzyl or phenethyl; and
each of R2 and R3 independent of the other is hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, trifluoromethyl, alkanoyl of 2 to 4 carbon atoms, amino, alkanoylamino of 2 to 4 carbon atoms or carbalkoxy of 2 to 7 carbon atoms.
3. A compound according to claim 2 which is an N-(4-phenylthio-2-amidophenyl)guanidine as therein defined.
4. A compound according to claim 3 wherein R4 is alkyl of 1 to 6 carbon atoms or alkoxyalkyl of 2 to 8 carbon atoms, R5 is alkyl of 1 to 4 carbon atoms, and R6 is alkoxy of 1 to 4 carbon atoms.
5. A compound according to claim 2 which is an N-(5-phenylthio-2-amidophenyl)guanidine as therein defined.
6. A compound according to claim 5 wherein R4 is alkyl of 1 to 6 carbon atoms or alkoxyalkyl of 2 to 8 carbon atoms, R5 is alkyl of 1 to 4 carbon atoms, and R6 is alkoxy of 1 to 4 carbon atoms.
7. The compound according to claim 1 which as the formula: ##SPC27## ##SPC28##
8. The compound according to claim 1 which has the formula: ##SPC29##
9. The compound according to claim 1 which has the formula: ##SPC30##
10. The compound according to claim 1 which has the formula: ##SPC31##
11. The compound according to claim 1 which has the formula: ##SPC32##
Description
DETAILED DESCRIPTION

The present invention pertains to substituted phenylguanidines, to methods for their preparation and use as anthelmintics, and to compositions thereof useful in such use.

Various N-formyl- and N-alkanamido-N',N"-bis(carbalkoxy)guanidines are described in German Offenlegungschrift No. 2,117,293 as having anthelmintic properties. The effect of these properties however is relatively weak.

The present invention pertains to anthelmintic phenylguanidines of the formula: ##SPC1##

Wherein

X is oxygen, sulfur, sulfinyl or sulfonyl; one of R and R1 is --COR4 and the other is ##STR1## in which R4 is hydrogen or an unsubstituted or substituted alkyl, cycloalkyl, alkoxy, aryl or amino group;

R5 is an unsubstituted or substituted alkyl, alkenyl or alkynyl group; and

R6 is hydrogen or an unsubstituted or substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, alkoxy, alkenyloxy or alkynyloxy group; and

Each of R2 and R3 independent of the other is hydrogen, halogeno, cyano, or an unsubstituted or substituted alkyl, alkoxy, alkylthio, halogenoalkyl, amino or carbalkoxy group.

The foregoing guanidines can be depicted in several tautomeric forms, as shown below for the guanidine moiety only: ##STR2##

While for consistency and conciseness the structural formulas have been shown in only one of the foregoing ways, it will be appreciated that the actual compounds are inclusive of all tautomeric forms.

In the present context, the optionally-substituted alkyl groups embraced by R2, R3, R4, R5 and R6 are straight- or branched hydrocarbon chains containing from 1 to 6, especially from 1 to 4, carbon atoms, as for example methyl, ethyl, n- and i-propyl, and n-, i- and t-butyl groups.

Alkenyl groups embraced by R5 and R6 will be straight- or branched chained and contain from 2 to 6, especially 2 to 4, carbon atoms. Ethenyl, propenyl-(1), propenyl-(2) and butenyl-( 3) can be mentioned as examples.

Alkynyl groups embraced by R5 and R6 will be straight- or branched chained and contain from 2 to 6, especially from 2 to 4, carbon atoms. Ethynyl, propynyl-(1), propynyl-(2) and butynyl-(3) are typical.

Alkoxy groups embraced by R2, R3, R4 and R6 are straight- or branched chained with from 1 to 6, especially from 1 to 4, carbon atoms. Methoxy, ethoxy, n- and i-propoxy and n-, i- and t-butoxy may be mentioned as examples.

Alkylthio groups embraced by R2 and R3 are straight- or branched chained with from 1 to 6, especially from 1 to 4, carbon atoms. Methylthio, ethylthio, n- and i-propylthio and n-, i- and t-butylthio may be mentioned as examples.

Alkanoyl groups embraced by R2 and R3, alone or in combination as in alkanoylamino, contain from 1 to 6, especially 2 to 4, carbon atoms. Formyl, acetyl, propionyl, n-butyryl and i-butyryl can be mentioned as examples of alkanoyl.

Carbalkoxy groups embraced by R2 and R3 can be straight or branched chained with from 2 to 7, especially 2 to 5, carbon atoms. Carbomethoxy, carbethoxy, carbo-n- and i-propoxy and carbo-n-, -i- and -t-butoxy can be mentioned as examples.

The halogenalkyl groups embraced by R2 and R3 contain from 1 to 4, especially 1 or 2, carbon atoms and preferably from 1 to 5, especially 1 to 3, identical or different halogen atoms, the halogen atoms being fluorine, chlorine and bromine, especially fluorine and chlorine. Perhalogenated alkyl groups are preferred. Trifluoromethyl, chlorodifluoromethyl, bromomethyl, 2,2,2-trifluoroethyl and pentafluoroethyl can be mentioned as examples.

Halogeno embraced by R2 and R3 is fluoro, chloro, bromo or iodo, especially fluoro, chloro and bromo.

Aryl groups embraced by R4 and R6 contain from 6 to 10 carbon atoms in the aromatic ring system. Optionally-substituted phenyl and naphthyl can be mentioned as examples.

Aralkyl groups embraced by R4 and R6 are optionally-substituted in the aryl part or alkyl part with 6 to 10, preferably 6, carbon atoms in the aryl part and from 1 to 4, especially 1 or 2, carbon atoms in the alkyl part. The alkyl part can be straight- or branched chained. Optionally-substituted benzyl and phenylethyl are typical.

Cycloalkyl groups embraced by R4 and R6 are monocyclic, bicyclic or tricyclic cycloalkyl groups with from 3 to 10, especially 3 to 6, carbon atoms. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl cycloheptyl bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and adamantyl are examples.

Alkenyloxy groups embraced by R6 are straight- or branched chained from 2 to 6, especially 2 to 4, carbon atoms. Ethenyloxy, propenyl-(1)-oxy, propenyl-(2)-oxy and butenyl-(3)-oxy are examples.

Alkynyloxy groups embraced by R6 are straight- or branched chained with from 2 to 6, especially 2 to 4, carbon atoms. Ethynyloxy, propynyl-(1)-oxy, propynyl-(2)-oxy and butynyl-(3)-oxy are examples.

The foregoing groups embraced by R2, R3, R4, R5 and R6, other than hydrogen and halogeno, can in turn be optionally substituted as for example by acyl with 2 to 4 carbon atoms, carbalkoxy groups with 2 to 4 carbon atoms, alkoxyalkyl groups with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, and aralkyl groups with 1 to 4 carbon atoms in the alkyl part and 6 carbon atoms in the aryl part.

Particularly preferred compounds are those in which

R2 and R3 are each independently hydrogen, methyl, ethyl, n-butyl, methoxy or ethoxy, fluoro, chloro, bromo, cyano, methylmercapto, trifluoromethyl, acetyl, propionyl, acetylamino or carbmethoxyamino;

R4 is methyl, ethyl, propyl, n-butyl, i-butyl, n-pentyl, n-hexyl, cyclopentyl, cyclohexyl, phenyl, benzyl, methoxymethyl, methoxy, ethoxy, phenoxymethyl, methylamino, ethylamino, n-butylamino, n-cyanopentylamino or β-methoxyethylamino;

R5 is methyl, ethyl, i-propyl, sec.-butyl, propenyl-(2) or propinyl; and

R6 is methyl, ethyl, propyl, isopropyl, n-amyl, isoamyl, n-butyl, cyclohexyl, benzyl, methoxymethyl, phenoxymethyl, allyl, crotyl, methallyl, methoxy, ethoxy, i-propoxy, sec.-butoxy, propenyl-(2)-oxy, propynyl-(2)-oxy, or 2-methyl-propenyl-(2)-oxy.

The compounds are prepared by a process which comprises (a.) reacting a compound of the formula: ##SPC2##

wherein R2, R3 and R4 are as defined above,

with an isothiourea-S-alkyl ether of the formula: ##STR3## in the presence of an acid and in an inert organic solvent, or (b.) treating a compound of the formula: ##SPC3##

wherein R, R1, R2 and R3 are as defined above and X is sulfur with an oxidizing agent to yield the corresponding compound wherein X is sulfinyl or sulfonyl.

The first of the foregoing two reactions is generally conducted in an inert organic solvent, generally a polar solvent such as an alcohol, as for example methanol, ethanol or isopropanol, a ketone such as acetone or methylethyl ketone, an alkanoic acid such as acetic acid, an ether such as ethyl ether and tetrahydrofuran. The medium may be aqueous, utilizing one of the foregoing water-miscible solvents in combination with water. The reaction is carried out at a temperature of from 0 to 120 C, preferably from 30 to 100 C, preferably at the boiling point of the solvent, in the presence of an organic or inorganic acid such as hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetic acid, p-toluenesulfonic acid, and the like. Equimolar amounts of reactants are generally employed although this can vary by about 20% without significant effect on the yield. An alkylmercaptan is formed as a by-product and the desired product is obtained by cooling the reaction mixture and collecting the solid which can be purified if desired by conventional techniques such as recrystallization.

In the foregoing second reaction, a compound of the present invention wherein X is sulfur is treated with one molar equivalent of an oxidizing agent to yield the corresponding compound where X is sulfinyl or with two moles to yield the corresponding compound where X is sulfonyl. The oxidizing agents include organic peroxoacids, such as peracetic acid, performic acid, perbenzoic acid, m-chlorobenzoic acid, monoperphthalic acid and the like; inorganic peroxides, such as hydrogen peroxide; organic acids dissolved in water or otherwise diluted; inorganic oxidation agents such as chromic acid, nitric acid, potassium permanganate, chlorine or bromine; halo oxy acids such as hypochlorous acid, chlorous acid, chloric acid, perchloric acid, tert.-butyl hypochlorite, methyl hypochlorite, tert.-butylchromate and the like; or N-haloimides such as N-chloro-succinimide and N-bromosuccinimide, N-halo sulphonic acid amides or N-halo carboxylic acid amides.

Reaction conditions are selected, in a manner known to the art, so that oxidation potential is adjusted for the production of either sulfoxides or sulfones.

Many of the thioureas used as starting materials in the first reaction are known (see Olin and Dains, J. Amer. Chem. Soc. 52, 3326 (1930) and U.S. Pat. No. 2,993,502) while others can easily be obtained by known processes. The thioureas are generally prepared from known N-acylthioureas [see, e.g. "Berichte der deutschen Chemischen Gesellschaft", 6, 755 (1873); Ann, Chim. (5) 11, 313 (1877); J. Amer. Chem. Soc. 62, 3274 (1940)], which are reacted with alkylating agents such as alkyl halides, alkyl sulphates or alkyl sulphonates to give the corresponding S-alkyl-N-acyl-isothioureas [see, e.g. J. Org. Chem. 30, 560, (1965); Chem. Pharm. Bull. (Tokyo), 9, 245, (1961)]. These S-alkyl-N-acyl-isothioureas are then reacted with halogenoformic acid esters or with pyrocarbonic acid dialkyl esters [see, e.g. Ber. dtsch, chem. Ges. 71, 1797 (1938)] to give the S-alkyl-N-acyl-N'-alkoxycarbonyl-isothioureas, which corresponds to the known substitution of S-alkylisothioureas with chloroformic acid alkyl esters [see, e.g. J. Amer. Chem. Soc. 52, 3326 (1930 )].

The following are typical isothioureas which can be employed in accordance with the process of this invention: N,N'-bis-methoxycarbonyl-S-methyl-isothiourea (melting point 99-100 C), N,N'-bis-ethoxycarbonyl-S-methyl-isothiourea (melting point 50-51 C), N-ethoxycarbonyl-N'-propionyl-S-methyl-isothiourea (melting point 92-94 C), N-methoxycarbonyl-N'-propionyl-S-methyl-isothiourea (melting point 97-99 C), N-methoxycarbonyl-N'-ethoxyacetyl-S-methyl-isothiourea (melting point 69-70 C), N-methoxycarbonyl-N' -cyclohexylcarbonyl-S-methyl-isothiourea (m.p. 67-68 C), N-methoxycarbonyl-N'-phenylacetyl-S-methyl-isothiourea (m.p. 55-56 C), N-ethoxycarbonyl-N'-benzoyl-S-methyl-isothiourea (m.p. 79-80 C), N-ethoxycarbonyl-N'-methoxycarbonyl-S-methylisothiourea (m.p. 69 C), N-allyloxycarbonyl-N'-methoxycarbonyl-S-methyl-isothiourea, N-propinyloxycarbonyl-N'-methoxycarbonyl-S-methyl-isothiourea, N,N'-bis-allyloxycarbonyl-S-methyl-isothiourea and N,N'-bis-propinyloxycarbonyl-S-methyl-isothiourea.

Most of the 2-aminoanilide starting materials are known. Those that are not previously known can be readily prepared by methods analogous to those disclosed in the literature. For example, a 2-nitroaniline having the appropriate substituent in the 4- or 5-position, e.g., phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, can be N-acylated with an acid chloride of the formula R4 COCl to yield the corresponding 2-nitro-4- or 5-substituted anilide which is hydrogenated as with Raney nickel to yield the 2-amino-4- or 5-substituted anilide. The 2-nitroanilines having a phenylsulfinyl or phenylsulfonyl group in the 4- or 5-positions can also be obtained from the corresponding phenylthio compounds through controlled oxidation analogous to that described above, e.g. using hydrogen peroxide in acetic anhydride or perbenzoic acid in dioxane or chloroform, to yield the sulfinyl compound, or hydrogen peroxide in glacial acetic acid to yield the sulfone. The 4- and 5-phenylsulfonyl-2-nitroanilines can also be obtained by the reaction of a sodiumbenzenesulfinate with a 4- or 5-chloro-2-nitroaniline as for example dimethylformamide at about 140 C.

The following may be mentioned as examples of the 2-amino-anilides employed as starting materials: 2-amino-5-phenoxy-acetanilide, 2-amino-5-phenoxy-propionanilide, 2-amino-5-phenoxy-butyranilide, 2-amino-5-phenoxy-iso-butyranilide, 2-amino-5-phenoxy-valeranilide, 2-amino-5-phenoxy-iso-valeranilide, 2-amino-5-phenoxy-caproanilide, 2-amino-5-phenoxy-iso-caproanilide, 2-amino-5-phenoxy-cyclopentanecarboxylic acid anilide, 2-amino-5-phenoxy-cyclohexanecarboxylic acid anilide, 2-amino-5-phenoxy-phenylacetanilide, 2-amino-5-phenoxy-phenoxyacetanilide, 2-amino-5-phenoxy-benzanilide, N-(2-amino-5-phenoxy-phenyl)-N'-methyl-urea, N-(2-amino-5-phenoxy-phenyl)-N'-ethyl-urea, N-(2-amino-5-phenoxy-phenyl)-N'-butyl-urea, N-(2-amino-5-phenoxy-phenyl)-N'-ω-cyanopentyl-urea, N-(2-amino-5-phenoxy-phenyl)-N'-β-methoxyethyl-urea, N-(2-amino-5-phenoxy-phenyl)-N'-benzyl-urea, N-(2-amino-5-phenoxy-phenyl)-N'-phenyl-urea, 2-amino-5-(4-methyl-phenoxy)-propionanilide, 2-amino-5-(4-methyl-phenoxy)-butyranilide, 2-amino-5-(4-methyl-phenoxy)-acetanilide, 2-amino-5-(3-methyl-phenoxy)-propionanilide, 2-amino-5-(3-methyl-phenoxy)-butryanilide, 2-amino-5-(3-methyl-phenoxy)-acetanilide, 2-amino-5-(2-methyl-phenoxy)-propionanilide, 2-amino-5-(2-methyl-phenoxy)-butyranilide, 2-amino-5-(2-methyl-phenoxy)-acetanilide, 2-amino-5-(4-chloro-phenoxy)-propionanilide, 2-amino-5-(4-chloro-phenoxy)-butyranilide, 2-amino-5-(4-chloro-phenoxy)-acetanilide, 2-amino-5-(3-chloro-phenoxy)-propionanilide, 2-amino-5-(3-chloro-phenoxy)-butyranilide, 2-amino-5-(3-chloro-phenoxy)-acetanilide, 2-amino-5-(2-chloro-phenoxy)-propionanilide, 2-amino-5-(2-chloro-phenoxy)-butyranilide, 2-amino-5-(2-chloro-phenoxy)-acetanilide, 2-amino-5-(4-methoxy-phenoxy)-propionanilide, 2-amino-5-(4-methoxy-phenoxy)-butyranilide, 2-amino-5-(4-methoxy-phenoxy)-acetanilide, 2-amino-5-(3-methoxy-phenoxy)-propionanilide, 2-amino-5-(3-methoxy-phenoxy)-butyranilide, 2-amino-5-(3-methoxy-phenoxy)-acetanilide, 2-amino-5-(4-methylthio-phenoxy)-propionanilide, 2-amino-5-(4-methylthio-phenoxy)-butyranilide, 2-amino-5-(4-methylthio-phenoxy)-acetanilide, 2-amino-5-(3-methylthio-phenoxy)-propionanilide, 2-amino-5-(3-methylthio-phenoxy)-butyranilide, 2-amino-5-(3-methylthio-phenoxy)-acetanilide, 2-amino-5-(4-cyano-phenoxy)-propionanilide, 2-amino-5-(4-cyano-phenoxy)-butyranilide, 2-amino-5-(4-ayano-phenoxy)acetanilide, 2-amino-5-(3-cyano-phenoxy)-propionanilide, 2-amino-5-(3-cyano-phenoxy)-butyranilide, 2-amino-5-(3-cyano-phenoxy)-acetanilide, 2-amino-5-(4-acetyl-phenoxy)-propionanilide, 2-amino-5-(4-acetyl-phenoxy)-butyranilide, 2-amino-5-(4-acetyl-phenoxy)-acetanilide, 2-amino-5-(4-propionyl-phenoxy)-propionanilide, 2-amino-5-(4-propionyl-phenoxy)-butyranilide, 2-amino-5-(4-propionyl-phenoxy)-acetanilide, 2-amino-5-(4-acetylamino-phenoxy)-propionanilide, 2-amino-5-(4-acetylamino-phenoxy)-butyranilide, 2-amino-5-(4-acetylamino-phenoxy)-acetanilide, 2-amino-5-(4-methoxycarbonylamino-phenoxy)-propionanilide, 2-amino-5-(4-methoxycarbonylamino-phenoxy)-butyranilide, 2-amino-5-(4-methoxycarbonylamino-phenoxy)-acetanilide, 2-amino-5-(4-methoxycarbonyl-phenoxy)-propionanilide, 2-amino-5-(4-methoxycarbonyl-phenoxy)-butyranilide, 2 -amino-5-(4-methoxycarbonyl-phenoxy)-acetanilide, 2-amino-5-(3,4-dimethyl-phenoxy)-propionanilide, 2-amino-5-(3,4-dimethyl-phenoxy)-butyranilide, 2-amino-5-(3,4-dimethyl-phenoxy)-acetanilide, 2-amino-5-(2-methyl-4-chloro-phenoxy)-propionanilide, 2-amino-5-(2-methyl-4-chloro-phenoxy)-butyranilide, 2-amino-5-(2-methyl-4-chloro-phenoxy)-acetanilide, 2-amino-5-(4-ethyl-phenoxy)-propionanilide, 2-amino-5-(4-ethyl-phenoxy)-butyranilide, 2-amino-5-(4-ethyl-phenoxy)-acetanilide, 2-amino-5-(3,4-dichloro-phenoxy)-propionanilide, 2-amino-5-(3,4-dichloro-phenoxy)-butyranilide, 2-amino-5-(3,4-dichloro-phenoxy)-acetanilide, 2-amino-5-(4-bromo-phenoxy)-propionanilide, 2-amino-5-(4-bromo-phenoxy)-butyranilide, 2-amino-5-(4-bromo-phenoxy)-acetanilide, 2-amino-5-(3,5-dimethyl-phenoxy)-propionanilide, 2-amino-5-(dimethyl-phenoxy)-butyranilide, 2-amino-5-(3,5-dimethyl-phenoxy)-acetanilide, 2-amino-5-(4-butyl-phenoxy)-propionanilide, 2-amino-5-(4-butyl-phenoxy)-butyranilide, 2-amino-5-(4-butyl-phenoxy)-acetanilide, 2-amino-5-(3-butyl-phenoxy)-propionanilide, 2-amino-5-(3-butyl-phenoxy)-butyranilide, 2-amino-5-(3-butyl-phenoxy)-acetanilide, 2-amino-4-phenoxy-acetanilide, 2-amino-4-phenoxy-propionanilide, 2-amino-4-phenoxy-butyranilide, 2-amino-4-phenoxy-iso-butyranilide, 2-amino-4-phenoxy-valeranilide, 2-amino-4-phenoxy-iso-valeranilide, 2-amino-4-phenoxy-caproanilide, 2-amino-4-phenoxy-iso-capronanilide, 2-amino-4-phenoxy-cyclopentanecarboxylic acid anilide, 2-amino-4-phenoxy-cyclohexanecarboxylic acid anilide, 2-amino-4-phenoxy-phenylacetanilide, 2-amino-4-phenoxy-phenoxyacetanilide, 2-amino-4-phenoxy-benzanilide, N-(2-amino-4-phenoxy-phenyl)-N'-methyl-urea, N-(2-amino-4-phenoxy-phenyl)-N'-ethyl-urea, N-(2-amino-4-phenoxy-phenyl)-N'-butyl-urea, N-(2-amino-4-phenoxy-phenyl)-N'-ω-cyanopentyl-urea N-(2-amino-4-phenoxy-phenyl)-N'-β-methoxyethyl-urea, N-(2-amino- 4-phenoxy-phenyl)-N'-benzyl-urea, N-(2-amino-4-phenoxy-phenyl)-N'-phenyl-urea, 2-amino-4-(4-methyl-phenoxy)-propionanilide, 2-amino-4-(4-methyl-phenoxy)-butyranilide, 2-amino-4-(4-methyl-phenoxy)-acetanilide, 2-amino-4-(3-methyl-phenoxy)-propionanilide, 2-amino-4-(3-methyl-phenoxy)-butyranilide, 2-amino-4-(3-methyl-phenoxy)-acetanilide, 2-amino-4-(2-methyl-phenoxy)-propionanilide, 2-amino-4-(2-methyl-phenoxy)-butyranilide, 2-amino-4-(2-methyl-phenoxy)-acetanilide, 2-amino-4-(4-chloro-phenoxy)-propionanilide, 2-amino-4-(4-chloro-phenoxy)-butyranilide, 2-amino-4-(4-chloro-phenoxy)-acetanilide, 2-amino-4-(3-chloro-phenoxy)-propionanilide, 2-amino-4-(3-chloro-phenoxy)-butyranilide, 2-amino-4-(3-chloro-phenoxy)-acetanilide, 2-amino-4-(2-chloro-phenoxy)-propionanilide, 2-amino-4-(2-chloro-phenoxy)-butyranilide, 2-amino-4-(2-chloro-phenoxy)-acetanilide, 2-amino-4-(4-methoxy-phenoxy)-propionanilide, 2-amino-4-(4-methoxy-phenoxy)-butyranilide, 2-amino-4-(4-methoxy-phenoxy)-acetanilide, 2-amino-4-(3-methoxy-phenoxy)-propionanilide, 2-amino-4-(3-methoxy-phenoxy)-butyranilide, 2-amino-4-(3-methoxy-phenoxy)-acetanilide, 2-amino-4-(4-methylthio-phenoxy)-propionanilide, 2-amino-4-(4-methylthio-phenoxy)-butyranilide, 2-amino-4-(4-methylthio-phenoxy)-acetanilide, 2-amino-4-(3-methylthio-phenoxy)-propionanilide, 2-amino-4-(3-methylthio-phenoxy)-butyranilide, 2-amino-4-(3-methylthio-phenoxy)-acetanilide, 2-amino-4-(4-cyano-phenoxy)-propionanilide, 2-amino-4-(4-cyano-phenoxy)-butyranilide, 2-amino-4-(4-cyano-phenoxy)-acetanilide, 2-amino-4-(3-cyano-phenoxy)-propionanilide, 2-amino-4-(3-cyano-phenoxy)-butyranilide, 2-amino-4-(3-cyano-phenoxy)-acetanilide, 2-amino-4-(4-acetyl-phenoxy)-propionanilide, 2-amino- 4-(4-acetyl-phenoxy)-butyranilide, 2 -amino-4-(4-acetyl-phenoxy)-acetanilide, 2-amino-4-(4-propionyl-phenoxy)-propionanilide, 2-amino-4-(4-propionyl-phenoxy)-butyranilide, 2-amino-4-(4-propionyl-phenoxy)-acetanilide, 2-amino-4-(4-acetaylamino-phenoxy)-propionanilide, 2-amino-4-(4-acetylamino-phenoxy)-butyranilide, 2-amino-4-(4-acetylamino-phenoxy)acetanilide, 2-amino-4-(4-methoxycarbonylamino-phenoxy)-propionanilide, 2-amino-4-(4-methoxycarbonylamino-phenoxy)-butyranilide, 2-amino-4-(4-methoxycarbonylamino-phenoxy)-acetanilide, 2-amino-4-(4-methoxycarbonyl-phenoxy)-propionanilide, 2-amino-4-(4-methoxycarbonyl-phenoxy)-butyranilide, 2-amino-4-(4-methoxycarbonyl-phenoxy)-acetanilide, 2-amino-4-(3,4-dimethyl-phenoxy)-propionanilide, 2-amino-4-(3,4-dimethyl-phenoxy)-butyranilide, 2-amino-4-(3,4-dimethyl-phenoxy)-acetanilide, 2-amino-4-(2-methyl-4-chloro-phenoxy)-propionanilide, 2-amino-4-(2-methyl-4-chloro-phenoxy)-butyranilide, 2-amino-4-(2-methyl-4-chloro-phenoxy)-acetanilide, 2-amino-4-(4-ethyl-phenoxy)-propionanilide, 2-amino-4-(4-ethyl-phenoxy)-butyranilide, 2-amino-4-(4-ethyl-phenoxy)-acetanilide, 2-amino-4-(3,4-dichloro-phenoxy)-propionanilide, 2-amino-4-(3,4-dichloro-phenoxy)-butyranilide, 2-amino-4-(3,4-dichloro-phenoxy)-acetanilide, 2-amino-4-(4-bromo-phenoxy)-propionanilide, 2-amino-4-(4-bromo-phenoxy)-butyranilide, 2-amino-4-(4-bromo-phenoxy)-acetanilide, 2-amino-4-(3,5-dimethyl-phenoxy)-propionanilide, 2-amino-4-(3,5-dimethyl-phenoxy)-butyranilide, 2-amino-4-(3,5-dimethyl-phenoxy)-acetanilide, 2-amino-4-(4-butyl-phenoxy)-propionanilide, 2-amino-4-(4-butyl-phenoxy)-butyranilide, 2-amino-4-(4-butyl-phenoxy)-acetanilide, 2-amino-4-(3-butyl-phenoxy)-propionanilide, 2-amino-4-(3-butyl-phenoxy)-butyranilide, 2-amino-4-(3-butyl-phenoxy)-acetanilide, 2-amino-5-phenylthio-acetanilide, 2-amino-5-phenylthio-propionanilide, 2 -amino-5-phenylthio-butyranilide, 2-amino-5-phenylthio-iso-butyranilide, 2-amino-5-phenylthio-valeranilide, 2-amino-5-phenylthio-iso-valeranilide, 2-amino-5-phenylthio-caproanilide, 2-amino-5-phenylthio-iso-caproanilide, 2-amino-5-phenylthio-cyclopentanecarboxylic acid anilide, 2-amino-5-phenylthio-cyclohexanecarboxylic acid anilide, 2-amino-5-phenylthio-phenylacetanilide, 2-amino-5-phenylthio-phenoxyacetanilide, 2-amino-5-phenylthio-benzanilide, N-(2-amino-5-phenylthio-phenyl)-N'-methyl-urea, 2-amino-5-phenylthio-methoxyacetanilid, N-(2-amino-5-phenylthio-phenyl)-N'-butyl-urea, N-(2-amino-5-phenylthio-phenyl)-N'-ω-cyanopentyl-urea, N-(2-amino-5-phenylthio-phenyl)-N'-β-methoxyethyl-urea, N-(2-amino-5-phenylthio-phenyl)-N'-benzyl-urea, N-(2-amino-5-phenylthio-phenyl)-N'-phenyl-urea, 2-amino-5-(4-methyl-phenylthio)-propionanilide, 2-amino-5-(4-methyl-phenylthio)-butyranilide, 2-amino-5-(4-methyl-phenylthio)-acetanilide, 2-amino-5-(3-methyl-phenylthio)-propionanilide, 2-amino-5-(3-methyl-phenylthio)-butyranilide, 2-amino-5-(3-methyl-phenylthio)-acetanilide, 2-amino-5-(2-methyl-phenylthio)-propionanilide, 2-amino-5-(2-methyl-phenylthio)-butyranilide, 2-amino-5-(2-methyl-phenylthio)-acetanilide, 2-amino-5-(4-chloro-phenylthio)-propionanilide, 2-amino-5-(4-chloro-phenylthio)-butyranilide, 2-amino-5-(4-chloro-phenylthio)-acetanilide, 2-amino-5-(3-chloro-phenylthio)-propionanilide, 2-amino-5-(3-chloro-phenylthio)-butyranilide, 2-amino-5-(3-chloro-phenylthio)-acetanilide, 2-amino-5-(2-chloro-phenylthio)-propionanilide, 2-amino-5-(2-chloro-phenylthio)-butyranilide, 2-amino-5-(2-chloro-phenylthio)-acetanilide, 2-amino-5-(4-methoxy-phenylthio)-propionanilide, 2-amino-5-(4-methoxy-phenylthio)-butyranilide, 2-amino-5-(4-methoxy-phenylthio)-acetanilide, 2-amino-5-(3-methoxy-phenylthio)-propionanilide, 2-amino-5-(3-methoxy-phenylthio)-butyranilide, 2-amino-5-(3-methoxy-phenylthio)-acetanilide, 2-amino- 5-(4-methylthio-phenylthio)-propionanilide, 2-amino-5-(4-methylthio-phenylthio)-butyranilide, 2amino-5-(4-methylthio-phenylthio)-acetanilide, 2-amino-5-(3-methylthio-phenylthio)-propionanilide, 2-amino-5-(3-methylthio-phenylthio)-propionanilide, 2-amino-5-(3-methylthio-phenylthio)-butyranilide, 2-amino-5-(3-methylthio-phenylthio)-acetanilide, 2-amino-5-(4-cyano-phenylthio)-propionanilide, 2-amino-5-(4-cyano-phenylthio)-butyranilide, 2-amino-5-(4-cyano-phenylthio)-acetanilide, 2-amino-5-(3-cyano-phenylthio)-propionanilide, 2-amino-5-(3-cyano-phenylthio)-butyranilide, 2-amino-5-(3-cyano-phenylthio)-acetanilide, 2-amino-5-(4-acetyl-phenylthio)-propionanilide, 2-amino-5-(4-acetyl-phenylthio)-butyranilide, 2-amino-5-(4-acetyl-phenylthio)-acetanilide, 2-amino-5-(4-propionyl-phenylthio)-propionanilide, 2-amino-5-(4-propionyl-phenylthio)-butyranilide, 2-amino-5-(4-propionyl-phenylthio)-acetanilide, 2-amino-5-(4-acetylamino-phenylthio)-propionanilide, 2-amino-5-(4-acetylamino-phenylthio)-butyranilide, 2-amino-5-(4-acetylamino-phenylthio)-acetanilide, 2-amino-5-(4-methoxycarbonylamino-phenylthio)-propionanilide, 2-amino-5-(4-methoxycarbonylamino-phenylthio)-butyranilide, 2-amino-5-(4-methoxycarbonylamino-phenylthio)-acetanilide, 2-amino-5-(4-methoxycarbonyl-phenylthio)-propionanilide, 2-amino-5-(4-methoxycarbonyl-phenylthio)-butyranilide, 2-amino-5-(4-methoxycarbonyl-phenylthio)-acetanilide, 2-amino-5-(3,4-dimethyl-phenylthio)-propionanilide, 2-amino-5-(3,4-dimethyl-phenylthio)-butyranilide, 2-amino-5-(3,4-dimethyl-phenylthio)-acetanilide, 2-amino-5-(2-methyl-4-chloro-phenylthio)-propionanilide, 2-amino-5-(2-methyl-4-chloro-phenylthio)-butyranilide, 2-amino-5-(2-methyl-4-chloro-phenylthio)-acetanilide, 2-amino-5-(4-ethyl-phenylthio)-propionanilide, 2-amino-5-(4-ethyl-phenylthio)-butyranilide, 2-amino-5-(4-ethyl-phenylthio)-acetanilide, 2-amino-5-(3,4-dichloro-phenylthio)-propionanilide, 2-amino-5 -(3,4-dichloro-phenylthio)-butyranilide, 2-amino-5-(3,4-dichlorophenylthio)-acetanilide, 2-amino-5-(4-bromo-phenylthio)-propionanilide, 2-amino-5-(4-bromo-phenylthio)-butyranilide, 2-amino-5-(4-bromo-phenylthio)-acetanilide, 2-amino-5-(3,5-dimethyl-phenylthio)-propionanilide, 2-amino-5-(3,5-dimethylphenylthio)-butyranilide, 2-amino-5-(3,5-dimethyl-phenylthio)-acetanilide, 2-amino-5-(4-butyl-phenylthio)-propionanilide, 2-amino-5-(4-butyl-phenylthio)-butyranilide, 2-amino-5-(4-butylphenylthio)-acetanilide, 2-amino-5-(3-butyl-phenylthio)-propionanilide, 2-amino-5-(3-butyl-phenylthio)-butyranilide, 2-amino-5-(3-butyl-phenylthio)-acetanilide, 2-amino-4-phenylthio-acetanilide, 2-amino-4-phenylthio-propionanilide, 2-amino-4-phenylthio-butyranilide, 2-amino-4-phenylthio-iso-butyranilide, 2-amino-4-phenylthio-valeranilide, 2-amino-4-phenylthio-iso-valeranilide, 2-amino-4-phenylthio-caproanilide, 2-amino-4-phenylthio-iso-caproanilide, 2-amino-4-phenylthio-cyclopentanecarboxylic acid anilide, 2-amino-4-phenylthio-cyclohexanecarboxylic acid anilide, 2-amino-4-phenylthio-phenylacetanilide, 2-amino-4-phenylthio-phenoxyacetanilide, 2-amino-4-phenylthio-benzanilide, N-(2-amino-4-phenylthio-phenyl)-N'-methyl-urea, N-(2-amino-4-phenylthio-phenyl)-N'-methyl-urea, N-(2-amino-4-phenylthio-phenyl)-N'-butyl-urea, N-(2-amino-4-phenylthio-phenyl)-N'-ω-cyanopentyl-urea, N-(2-amino-4-phenylthio-phenyl)-N'-β-methoxyethyl-urea, N-(2-amino-4-phenylthio-phenyl)-N'-benzyl-urea, N-(2-amino-4-phenylthio-phenyl)-N'-phenyl-urea, 2-amino-4-(4-methyl-phenylthio)-propionanilide, 2-amino-4-(4-methyl-phenylthio)-butyranilide, 2-amino-4-(4-methyl-phenylthio)-acetanilide, 2-amino-4-(3-methyl-phenylthio)-propionanilide, 2-amino-4-(3-methyl-phenylthio)-butyranilide, 2-amino-4-(3-methyl-phenylthio)-acetanilide, 2-amino-4-(2-methyl-phenylthio)-propionanilide, 2-amino-4-(2-methyl-phenylthio)-butyranilide 2-amino-4-(2-methyl-phenylthio)-acetanilide, 2 -amino-4-(4-chloro-phenylthio)-propionanilide, 2-amino-4-(4-chloro-phenylthio)-butyranilide, 2-amino-4-(4-chloro-phenylthio)-acetanilide, 2-amino-4-(3-chloro-phenylthio)-propionanilide, 2-amino-4-(3-chloro-phenylthio)-butyranilide, 2-amino-4-(3-chloro-phenylthio)-acetanilide, 2-amino-4-(2-chloro-phenylthio)-propionanilide, 2-amino-4-(2-chlorophenylthio)-butyranilide, 2-amino-4-(2-chloro-phenylthio)-acetanilide, 2-amino-4-(4-methoxy-phenylthio)-propionanilide, 2-amino-4-(4-methoxy-phenylthio)-butyranilide, 2-amino-4-(4-methoxy-phenylthio)-acetanilide, 2-amino-4-(3-methoxy-phenylthio)-propionanilide, 2-amino-4-(3-methoxy-phenylthio)-butyranilide, 2-amino-4-(3-methoxy-phenylthio)-acetanilide, 2-amino-4-(4-methylthio-phenylthio)-propionanilide, 2-amino-4-(4-methylthio-phenylthio)-butyranilide, 2-amino-4-(4-methylthio-phenylthio)-acetanilide, 2-amino-4-(3-methylthio-phenylthio)-propionanilide, 2-amino-4-(3-methylthio-phenylthio)-butyranilide, 2-amino-4-(3-methylthio-phenylthio)-acetanilide, 2-amino-4-(4-cyano-phenylthio)-propionanilide, 2-amino-4-(4-cyano-phenylthio)-butyranilide, 2-amino-4-(4-cyano-phenylthio)-acetanilide, 2-amino-4-(3-cyano-phenylthio)-propionanilide, 2-amino-4-(3-cyano-phenylthio)-butyranilide, 2-amino-4-(3-cyano-phenylthio)-acetanilide, 2-amino-4-(4-acetyl-phenylthio)-propionanilide, 2-amino-4-(4-acetyl-phenylthio)-butyranilide, 2-amino-4-(4-acetyl-phenylthio)-acetanilide, 2-amino-4-(4-propionyl-phenylthio)-propionanilide, 2-amino-4-(4-propionyl-phenylthio)-butyranilide, 2-amino-4-(4-propionylphenylthio)-acetanilide, 2-amino-4-(4-acetylamino-phenylthio)-propionanilide, 2-amino-4-(4-acetylamino-phenylthio)-butyranilide, 2-amino-4-(4-acetylamino-phenylthio)-acetanilide, 2-amino-4-(4-methoxycarbonylamino-phenylthio)-propionanilide, 2-amino- 4-(4-methoxycarbonylamino-phenylthio)-butyranilide, 2-amino-4-(4-methoxycarbonylamino-phenylthio)-acetanilide, 2-amino-4-(4-methoxycarbonyl-phenylthio)-propionanilide, 2-amino-4-(4-methoxycarbonyl-phenylthio)-butyranilide, 2-amino-4-(4-methoxycarbonyl-phenylthio)-acetanilide, 2-amino-4-(3,4-dimethyl-phenylthio)-propionanilide, 2-amino-4-(3,4-dimethylphenylthio)-butyranilide, 2-amino-4-(3,4-dimethyl-phenylthio)-acetanilide, 2-amino-4-(2-methyl-4-chloro-phenylthio)-propionanilide, 2-amino-4-(2-methyl-4-chloro-phenylthio)-butyranilide, 2-amino-4-(2-methyl-4-chloro-phenylthio)-acetanilide, 2-amino-4-(4-ethyl-phenylthio)-propionanilide, 2-amino-4-(4-ethylphenylthio)-butyranilide, 2-amino-4-(4-ethyl-phenylthio)-acetanilide, 2-amino-4-(3,4-dichloro-phenylthio)-propionanilide, 2-amino-4-(3,4-dichloro-phenylthio)-butyranilide, 2-amino-4-(3,4-dichloro-phenylthio)-acetanilide, 2-amino-4-(4-bromo-phenylthio)-propionanilide, 2-amino-4-(4-bromo-phenylthio)-butyranilide, 2-amino-4-(4-bromo-phenylthio)-acetanilide, 2-amino-4-(3,5-dimethyl-phenylthio)-propionanilide, 2-amino-4-(3,5-dimethyl-phenylthio)-butyranilide, 2-amino-4-(3,5-dimethyl-phenylthio)-acetanilide, 2-amino-4-(4-butyl-phenylthio)-propionanilide, 2-amino-4-(4-butyl-phenylthio)-butyranilide, 2-amino-4-(4-butyl-phenylthio)-acetanilide, 2-amino-4-(3-butyl-phenylthio)-propionanilide, 2-amino-4-(3-butyl-phenylthio)-butyranilide, 2-amino-4-(3-butyl-phenylthio)-acetanilide, 2-amino-5-phenylsulphinyl-acetanilide, 2-amino-5-phenylsulphinyl-propionanilide, 2-amino-5-phenylsulphinyl-butyranilide, 2-amino-5-phenylsulphinyl-iso-butyranilide, 2-amino-5-phenylsulphinyl-valeranilide, 2-amino-5-phenylsulphinyl-iso-valeranilide, 2-amino-5-phenylsulphinyl-iso-caproanilide, 2-amino-5-phenylsulphinyl-cyclopentanecarboxylic acid anilide, 2-amino-5-phenylsulphinyl-cyclohexanecarboxylic acid anilide, 2-amino-5-phenylsulphinyl-phenylacetanilide, 2-amino- 5-phenylsulphinyl-phenoxyacetanilide, 2-amino-5-phenylsulphinylbenzanilide,N-(2-amino-5-phenylsulfinyl-phenyl)-N'-methyl-urea, 2-amino-5-phenylsulphinyl-methoxyacetanilid, N-(2-amino-5-phenylsulphinyl-phenyl)-N'-butyl-urea, N-(2-amino-5-phenylsulphinyl-phenyl)-N'-ω-cyanopentyl-urea, N-(2-amino-5-phenylsulphinyl-phenyl)-N'-β-methoxyethyl-urea, N-(2-amino-5-phenylsulphinyl-phenyl)-N'-benzyl-urea, N-(2-amino-5-phenylsulfinyl-phenyl)-N'-phenyl-urea, 2-amino-5-(4-methyl-phenylsulphinyl)-propionanilide, 2-amino-5-(4-methyl-phenylsulphinyl)-butyranilide, 2-amino-5-(4-methyl-phenylsulphinyl)-acetanilide, 2-amino-5-(3-methyl-phenylsulphinyl)-propionanilide, 2-amino-5-(3-methyl-phenylsulphinyl)-butyranilide, 2-amino-5-(3-methyl-phenylsulphinyl)-acetanilide, 2-amino-5-(2-methylphenylsulphinyl)-propionanilide, 2-amino-5-(2-methyl-phenylsulphinyl)-butyranilide, 2-amino-5-(2-methyl-phenylsulphinyl)-acetanilide, 2-amino-5-(4-chloro-phenylsulphinyl)-propionanilide, 2-amino-5-(4-chloro-phenylsulphinyl)-butyranilide, 2-amino-5-(4-chloro-phenylsulphinyl)-acetanilide, 2-amino-5-(3-chloro-phenylsulphinyl)-propionanilide, 2-amino-5-(3-chloro-phenylsulphinyl)-butyranilide, 2-amino-5-(3-chlorophenylsulphinyl)-acetanilide, 2-amino-5-(2-chloro-phenylsulphinyl)-propionanilide, 2-amino-5-(2-chloro-phenylsulphinyl)-butyranilide, 2-amino-5-(2-chloro-phenylsulphinyl)-acetanilide, 2-amino-5-(4-methoxy-phenylsulphinyl)-propionanilide, 2-amino-5-(4-methoxy-phenylsulphinyl)-butyranilide, 2-amino-5-(4-methoxy-phenylsulphinyl)-acetanilide, 2-amino-5-(3-methoxy-phenylsulphinyl)-propionanilide, 2-amino-5-(3-methoxy-phenylsulphinyl)-butyranilide, 2-amino-5-(3-methoxy-phenylsulphinyl)-acetanilide, 2-amino-5-(4-methylthio-phenylsulphinyl)-propionanilide, 2-amino-5-(4-methylthio-phenylsulphinyl)-butyranilide, 2-amino-5-(4-methylthio- phenylsulphinyl)-acetanilide, 2-amino-5-(3-methylthio-phenylsulphinyl)-propionanilide, 2-amino-5-(3-methylthio-phenylsulphinyl)-butyranilide, 2-amino-5-(3-methylthio-phenylsulphinyl)-acetanilide, 2-amino-5-(4-cyano-phenylsulphinyl)-propionanilide, 2-amino-5-(4-cyanophenylsulphinyl)-butyranilide, 2-amino-5-(4-cyano-phenylsulphinyl)-acetanilide, 2-amino-5-(3-cyano-phenylsulphinyl)-propionanilide, 2-amino-5-(3-cyano-phenylsulphinyl)-butyranilide, 2-amino-5-(3-cyano-phenylsulphinyl)-acetanilide, 2-amino-5-(4-acetyl-phenylsulphinyl)-propionanilide, 2-amino-5-(4-acetyl-phenylsulphinyl)-butyranilide, 2-amino-5-(4-acetylphenylsulphinyl)-acetanilide, 2-amino-5-(4-propionyl-phenylsulphinyl)-propionanilide, 2-amino-5-(4-propionyl-phenylsulphinyl)-butyranilide, 2-amino-5-(4-propionyl-phenylsulphinyl)-acetanilide, 2-amino-5-(4-acetylamino-phenylsulphinyl)-propionanilide, 2-amino-5-(4-acetylamino-phenylsulphinyl)-butyranilide, 2-amino-5-(4-acetylamino-phenylsulphinyl)-acetanilide, 2-amino-5-(4-methoxycarbonylamino-phenylsulphinyl)-propionanilide, 2-amino-5-(4-methoxycarbonylamino-phenylsulphinyl)-butyranilide, 2-amino-5-(4-methoxycarbonylamino-phenylsulphinyl)-acetanilide, 2-amino-5-(4-methoxycarbonyl-phenylsulphinyl)-propionanilide, 2-amino-5-(4-methoxycarbonyl-phenylsulphinyl)-butyranilide, 2-amino-5-(4-methoxycarbonyl-phenylsulphinyl)-acetanilide, 2-amino-5-(3,4-dimethyl-phenylsulphinyl)-propionanilide, 2-amino-5-(3,4-dimethyl-phenylsulphinyl)-butyranilide, 2-amino-5-(3,4-dimethyl-phenylsulphinyl)-acetanilide, 2-amino-5-(2-methyl-4-chloro-phenylsulphinyl)-propionanilide, 2-amino-5-(2-methyl-4-chloro-phenylsulphinyl)-butyranilide, 2-amino-5-(2-methyl-4-chloro-phenylsulphinyl)-acetanilide, 2-amino-5-(4-ethyl-phenylsulphinyl)-propionanilide, 2-amino-5-(4-ethyl-phenylsulphinyl)-butyranilide, 2-amino-5-(4-ethyl-phenylsulphinyl)-acetanilide, 2-amino-5-(3,4-dichloro-phenylsulphinyl)-propionanilide, 2-amino-5-(3,4-dichloro-phenylsulphinyl)-butyranilide, 2-amino-5-(3,4-dichloro-phenylsulphinyl)-acetanilide, 2-amino-5-(4-bromo-phenylsulphinyl)-propionanilide, 2-amino-5-(4-bromo-phenylsulphinyl)-butyranilide, 2-amino-5-(4-bromo-phenylsulphinyl)-acetanilide, 2-amino-5-(3,5-dimethyl-phenylsulphinyl)-propionanilide, 2-amino-5-(3,5-dimethyl-phenylsulphinyl)-butyranilide, 2-amino-5-(3,5-dimethyl-phenylsulphinyl)-acetanilide, 2-amino-5-(4-butyl-phenylsulphinyl)-propionanilide, 2-amino-5-(4-butyl-phenylsulphinyl)-butyranilide, 2-amino-5-(4-butylphenylsulphinyl)-acetanilide, 2-amino-5-(3-butyl-phenylsulphinyl)-propionanilide, 2-amino-5-(3-butyl-phenylsulphinyl)-butyranilide, 2-amino-5-(3-butyl-phenylsulphinyl)-acetanilide, 2-amino-4-phenylsulphinyl-acetanilide, 2-amino-4-phenylsulphinyl-propionanilide, 2-amino-4-phenylsulphinyl-butyranilide, 2-amino-4-phenylsulphinyl-iso-butyranilide, 2-amino-4-phenylsulphinyl-valeranilide, 2-amino-4-phenylsulphinyl-iso-valeranilide, 2-amino-4-phenylsulphinyl-caproanilide, 2-amino-4-phenylsulphinyl-iso-caproanilide, 2-amino-4-phenylsulphinylcyclopentanecarboxylic acid anilide, 2-amino-4-phenylsulphinyl-cyclohexanecarboxylic acid anilide, 2-amino-4-phenylsulphinyl-phenylacetanilide, 2-amino-4-phenylsulphinyl-phenoxyacetanilide, 2-amino-4-phenylsulphinyl-benzanilide, N-(2-amino-4-phenylsulphinyl-phenyl)-N'-methyl-urea, N-(2-amino-4-phenylsulphinyl-phenyl)-N'-ethyl-urea, N-(2-amino-4-phenylsulphinyl-phenyl)-N'-butyl-urea, N-(2-amino-4-phenylsulphinylphenyl)-N'-ω-cyanopentyl-urea, N-(2-amino-4-phenylsulphinylphenyl)-N'-β-methoxyethyl-urea, N-(2-amino-4-phenylsulphinylphenyl)-N'-benzyl-urea, N-(2-amino-4-phenylsulphinyl-phenyl)-N'-phenyl-urea, 2-amino-4-(4-methyl-phenylsulphinyl)-propionanilide, 2-amino-4-(4-methyl-phenylsulphinyl)-butyranilide, 2-amino-4-(4-methyl-phenylsulphinyl)-acetanilide, 2-amino-4-(3-methyl-phenylsulphinyl)-propionanilide, 2-amino-4-(3-methyl-phenylsulphinyl)-butyranilide, 2-amino-4-(3-methylphenylsulphinyl)-acetanilide, 2-amino-4-(2-methyl-phenylsulphinyl)-propionanilide, 2-amino-4-(2-methyl-phenylsulphinyl)-butyranilide, 2-amino-4-(2-methyl-phenylsulphinyl)-acetanilide, 2-amino-4-(4-chloro-phenylsulphinyl)-propionanilide, 2-amino- 4-(4-chloro-phenylsulphinyl)-butyranilide, 2-amino-4-(4-chloro-phenylsulphinyl)-acetanilide, 2-amino-4-(3-chlorophenylsulphinyl)-propionanilide, 2-amino-4-(3-chloro-phenylsulfinyl)-butyranilide, 2-amino-4-(3-chloro-phenylsulphinyl)-acetanilide, 2-amino-4-(2-chloro-phenylsulphinyl)-propionanilide, 2-amino-4-(2-chloro-phenylsulphinyl)-butyranilide, 2-amino-4-(2-chloro-phenylsulphinyl)-acetanilide, 2-amino-4-(4-methoxy-phenylsulphinyl)-propionanilide, 2-amino-4-(4-methoxy-phenylsulphinyl)-butyranilide, 2-amino-4-(4-methoxy-phenylsulphinyl)-acetanilide, 2-amino-4-(3-methoxy-phenylsulphinyl)- propionanilide, 2-amino-4-(3-methoxy-phenylsulphinyl)-butyranilide, 2-amino-4-(3-methoxy-phenylsulphinyl)-acetanilide, 2-amino-4-(4-methylthio-phenylsulphinyl)-propionanilide, 2-amino-4-(4-methylthio-phenylsulphinyl)-butyranilide, 2-amino-4(4-methylthio-phenylsulphinyl)-acetanilide, 2-amino-4-(3-methylthio-phenylsulphinyl)-propionanilide, 2-amino-4-(3-methylthio-phenylsulphinyl)-butyranilide, 2-amino-4-(3-methylthio-phenylsulphinyl)-acetanilide, 2-amino-4-(4-cyanophenylsulphinyl)-propionanilide, 2-amino-4-(4-cyano-phenylsulphinyl)-butyranilide, 2-amino-4-(4-cyano-phenylsulphinyl)-acetanilide, 2-amino-4-(3-cyano-phenylsulphinyl)-propionanilide, 2-amino-4-(3-cyano-phenylsulphinyl)-butyranilide, 2-amino-4-(3-cyano-phenylsulphinyl)-acetanilide, 2-amino-4-(4-acetyl-phenylsulphinyl)-propionanilide, 2-amino-4-(4-acetylphenylsulphinyl)-butyranilide, 2-amino- 4-(4-acetyl-phenylsulphinyl)-acetanilide, 2-amino-4-(4-propionyl-phenylsulphinyl)-propionanilide, 2-amino-4-(4-propionyl-phenylsulphinyl)- butyranilide, 2-amino-4-(4-propionyl-phenylsulphinyl)-acetanilide, 2-amino-4-(4-acetylamino-phenylsulphinyl)-propionanilide, 2-amino-4-(4-acetylamino-phenylsulphinyl)-butyranilide, 2-amino-4-(4-acetylamino-phenylsulphinyl)-acetanilide, 2-amino-4-(4-methoxycarbonylamino-phenylsulfinyl)-propionanilide, 2-amino-4-(4-methoxycarbonylamino-phenylsulphinyl)-butyranilide, 2-amino-4-(4-methoxycarbonylamino-phenylsulphinyl)-acetanilide, 2-amino-4-(4-methoxycarbonyl-phenylsulphinyl)-propionanilide, 2-amino-4-(4-methoxycarbonyl-phenylsulphinyl)-butyranilide, 2-amino-4-(4-methoxycarbonyl-phenylsulphinyl)-acetanilide, 2-amino-4-(3,4-dimethyl-phenylsulphinyl)-propionanilide, 2-amino-4-(3,4-dimethyl-phenylsulphinyl)-butyranilide, 2-amino-4-(3,4-dimethyl-phenylsulphinyl)-acetanilide, 2-amino-4-(2-methyl-4-chloro-phenylsulphinyl)-propionanilide, 2-amino-4-(2-methyl-4-chloro-phenylsulphinyl)-butyranilide, 2-amino-4-(2-methyl-4-chloro-phenylsulphinyl)-acetanilide, 2-amino-4-(4-ethyl-phenylsulphinyl)-propionanilide, 2-amino-4-(4-ethylphenylsulphinyl)-butyranilide, 2-amino-4-(4-ethyl-phenylsulphinyl)-acetanilide, 2-amino-4-(3,4-dichloro-phenylsulphinyl)-propionanilide, 2-amino-4-(3,4-dichloro-phenylsulphinyl)-butyranilide, 2-amino-4-(3,4-dichloro-phenylsulphinyl)-acetanilide, 2-amino-4-(4-bromo-phenylsulphinyl)-propionanilide, 2-amino-4-(4-bromo-phenylsulphinyl)-butyranilide, 2-amino-4-(4-bromo-phenylsulphinyl)-acetanilide, 2-amino-4-(3,5-dimethylphenylsulphinyl)-propionanilide, 2-amino-4-(3,5-dimethyl-phenylsulphinyl)-butyranilide, 2-amino-4-(3,5-dimethyl-phenylsulphinyl)-acetanilide, 2-amino-4-(4-butyl-phenylsulphinyl)-propionanilide, 2-amino-4-(4-butyl-phenylsulphinyl)-butyranilide, 2-amino-4-(4-butyl-phenylsulphinyl)-acetanilide, 2-amino-4-(3-butyl-phenylsulphinyl)-propionanilide, 2-amino-4-(3-butyl-phenylsulphinyl)-butyranilide, 2-amino-4-(3-butylphenylsulphinyl)-acetanilide, 2-amino-5-phenylsulphonyl-acetanilide, 2-amino-5-phenylsulphonyl-propionanilide, 2-amino-5-phenylsulphonyl-butyranilide, 2-amino-5-phenylsulphonyl-isobutyranilide, 2-amino-5-phenylsulphonyl-valeranilide, 2-amino-5-phenylsulfonyl-iso-valeranilide, 2-amino-5-phenylsulphonyl-caproanilide, 2-amino-5-phenylsulphonyl-iso-caproanilide, 2-amino-5-phenylsulphonyl-cyclopentanecarboxylic acid anilide, 2-amino-5-phenylsulphonyl-cyclohexanecarboxylic acid anilide, 2-amino-5-phenylsulphonyl-phenylacetanilide, 2-amino-5-phenylsulphonyl-phenoxyacetanilide, 2-amino-5-phenylsulphonyl-benzanilide, N-(2-amino-5-phenylsulphonyl-phenyl)-N'-methyl-urea, N-(2-amino-5-phenylsulphonyl-phenyl)-N'-ethyl-urea, N-(2-amino-5-phenylsulphonyl-phenyl)-N'-butyl-urea, N-(2-amino-5-phenylsulphonyl-phenyl)-N'-ω-cyanopentyl-urea, N-(2-amino-5-phenylsulphonyl-phenyl)-N'-β-methoxyethyl-urea, N-(2-amino-5-phenylsulphonyl-phenyl)-N'-benzyl-urea, N-(2-amino-5-phenylsulphonyl-phenyl)-N'-phenyl-urea, 2-amino-5-(4-methyl-phenylsulphonyl)-propionanilide, 2-amino-5-(4-methyl-phenylsulphonyl)-butyranilide, 2-amino-5-(4-methyl-phenylsulphonyl)-acetanilide, 2-amino-5-(3-methyl-phenylsulphonyl)-propionanilide, 2-amino-5-(3-methyl-phenylsulphonyl)-butyranilide, 2-amino-5-(4-methyl-phenylsulphonyl)-acetanilide, 2-amino-5-(3-methyl-phenylsulphonyl)-propionanilide, 2-amino-5-(3-methyl-phenylsulphonyl)-butyranilide, 2-amino-5-(3-methyl-phenylsulphonyl)-acetanilide, 2-amino-5-(2-methylphenylsulphonyl)-propionanilide, 2-amino-5-(2-methyl-phenylsulphonyl)-butyranilide, 2-amino-5-(2-methyl-phenylsulphonyl)-acetanilide, 2-amino-5-(4-chloro-phenylsulphonyl)-propionanilide, 2-amino-5-(4-chloro-phenylsulphonyl)-butyranilide, 2-amino-5-(4-chloro-phenylsulphonyl)-acetanilide, 2-amino-5-(3-chloro-phenylsulphonyl)-propionanilide, 2-amino-5-(3-chlorophenylsulphonyl)-butyranilide, 2-amino-5-(3-chloro-phenylsulphonyl)-acetanilide, 2-amino-5-(2-chloro-phenylsulphonyl)-propionanilide, 2-amino-5-(2-chloro-phenylsulphonyl)-butyranilide, 2-amino-5-(2-chloro-phenylsulphonyl)-acetanilide, 2-amino-5-(4-methoxy-phenylsulphonyl)-propionanilide, 2-amino-5-(4-methoxy-phenylsulphonyl)-butyranilide, 2-amino-5-(4-methoxy-phenylsulphonyl)-acetanilide, 2-amino-5-(3-methoxy-phenylsulphonyl)-propionanilide, 2-amino-5-(3-methoxy-phenylsulphonyl)-butyranilide, 2-amino-5-(3-methoxy-phenylsulphonyl)-acetanilide, 2-amino-5-(4-methylthio-phenylsulphonyl)-propionanilide, 2-amino-5-(4-methylthio-phenylsulphonyl)-butyranilide, 2-amino-5-(4-methylthio-phenylsulphonyl)-acetanilide, 2-amino-5-(3-methylthio-phenylsulphonyl)-propionanilide, 2-amino-5-(3-methylthio-phenylsulphonyl)-butyranilide, 2-amino-5-(3-methylthio-phenylsulphonyl)-acetanilide, 2-amino-5-(4-cyano-phenylsulphonyl)-propionanilide, 2-amino-5-(4-cyano-phenylsulphonyl)-butyranilide, 2-amino-5-(4-cyano-phenylsulphonyl)-acetanilide, 2-amino-5-(3-cyano-phenylsulphonyl)-propionanilide, 2-amino-5-(3-cyano-phenylsulphonyl)-butyranilide, 2-amino-5-(3-cyano-phenylsulphonyl)-acetanilide, 2-amino-5-(4-acetyl-phenylsulphonyl)-propionanilide, 2-amino-5-(4-acetyl-phenylsulphonyl)-butyranilide, 2-amino-5-(4-acetylphenylsulphonyl)-acetanilide, 2-amino-5-(4-propionyl-phenylsulphonyl)-propionanilide, 2-amino-5-(4-propionyl-phenylsulphonyl)-butyranilide, 2-amino-5-(4-propionyl-phenylsulphonyl)-acetanilide, 2-amino-5-(4-acetylamino-phenylsulphonyl)-propionanilide, 2-amino-5-(4-acetylamino-phenylsulphonyl)-butyranilide, 2-amino-5-(4-acetylamino-phenylsulphonyl)-acetanilide, 2-amino-5-(4-methoxycarbonylamino-phenylsulphonyl)-propionanilide, 2-amino-5-(4-methoxycarbonylamino-phenylsulphonyl)-butyranilide, 2-amino-5-(4-methoxycarbonylamino-phenylsulphonyl)-acetanilide, 2-amino-5-(4-methoxycarbonylphenylsulphonyl)-propionanilide, 2-amino-5 -(4-methoxycarbonylphenylsulphonyl)-butyranilide, 2-amino-5-(4-methoxycarbonylphenylsulphonyl)-acetanilide, 2-amino-5-(3,4-dimethyl-phenylsulphonyl)-propionanilide, 2-amino-5-(3,4-dimethyl-phenylsulphonyl)-butyranilide, 2-amino-5-(3,4-dimethyl-phenylsulphonyl)-acetanilide, 2-amino-5-(2-methyl-4-chloro-phenylsulphonyl)-acetanilide, 2-amino-5-(2-methyl-4-chloro-phenylsulphonyl)-propionanilide, 2-amino-5-(2-methyl-4-chloro-phenylsulphonyl)-butyranilide, 2-amino-5-(2-methyl-4-chloro-phenylsulphonyl)-acetanilide, 2-amino-5-(4-ethyl-phenylsulphonyl)-propionanilide, 2-amino-5-(4-ethyl-phenylsulphonyl)-butyranilide, 2-amino-5-(4-ethyl-phenylsulphonyl)-acetanilide, 2-amino-5-(3,4-dichloro-phenylsulphonyl)-propionanilide, 2-amino-5-(3,4-dichloro-phenylsulphonyl)-butyranilide, 2-amino-5-(3,4-dichloro-phenylsulphonyl)-acetanilide, 2-amino-5-(4-bromo-phenylsulphonyl)-propionanilide, 2-amino-5-(4-bromo-phenylsulphonyl)-butyranilide, 2-amino-5-(4-bromo-phenylsulphonyl)-acetanilide, 2-amino-5-(3,5-dimethyl-phenylsulphonyl)-butyranilide, 2-amino-5-(3,5-dimethyl-phenylsulphonyl)-acetanilide, 2-amino-5-(4-butyl-phenylsulphonyl)-propionanilide, 2-amino-5-(4-butyl-phenylsulphonyl)-butyranilide, 2-amino-5-(4-butyl-phenylsulphonyl)-acetanilide, 2-amino-5-(3-butyl-phenylsulphonyl)-propionanilide, 2-amino-5-(3-butyl-phenylsulphonyl)-butyranilide, 2-amino-5-(3-butyl-phenylsulphonyl)-acetanilide, 2-amino-4-phenylsulphonyl-acetanilide, 2-amino-4-phenylsulphonyl-propionanilide, 2-amino-4-phenylsulphonyl-butyranilide, 2-amino-4-phenylsulphonyl-iso-butyranilide, 2-amino-4-phenylsulphonyl-valeranilide, 2-amino-4-phenylsulphonyl-iso-valeranilide, 2-amino-4-phenylsulphonyl-caproanilide, 2-amino-4-phenylsulphonyl-iso-caproanilide, 2-amino-4-phenylsulphonyl-cyclopentanecarboxylic acid anilide, 2-amino-4-phenylsulphonyl-cyclohexanecarboxylic acid anilide, 2-amino-4-phenylsulphonyl-phenylacetanilide, 2-amino-4-phenylsulphonyl-phenoxyacetanilide, 2-amino-4-phenylsulphonyl-benzanilide, N-(2-amino-4-phonylsulphonyl-phenyl)-N'-phenylsulphonyl-phenyl)-N'N-(2-amino-4-phenylsulphonyl-phenyl)-N'-ethyl-urea, N-(2-amino-4-phenylsulphonyl-phenyl)-N'-butyl-urea, N-(2-amino-4-phenylsulphonyl-phenyl)-N'-ω-cyanopentyl-urea, N-(2-amino-4-phenylsulphonyl-phenyl)-N'-β-methoxyethyl-urea, N-(2-amino-4-phenylsulphonyl-phenyl)-N'-benzyl-urea, N-(2-amino-4-phenylsulphonyl-phenyl)-N'-phenyl-urea, 2-amin-4-(4-methyl-phenylsulphonyl)-propionanilide, 2-amino-4-(4-methyl-phenylsulphonyl)-butyranilide, 2-amino-4-(4-methyl-phenylsulphonyl)-acetanilide, 2-amino-4-(3-methyl-phenylsulphonyl)-propionanilide, 2-amino-4-(3-methyl-phenylsulphonyl)-butyranilide, 2-amino-4-(3-methyl-phenylsulphonyl)-acetanilide, 2-amino-4-(2-methyl-phenylsulphonyl)-propionanilide, 2-amino-4-(2-methyl-phenylsulphonyl)-butyranilide, 2-amino-4-(2-methyl-phenylsulphonyl)-acetanilide, 2-amino-4-(4-chloro-phenylsulphonyl)-propionanilide, 2-amino-4-(4-chloro-phenylsulphonyl)-butyranilide, 2-amino-4-(4-chloro-phenylsulphonyl)-acetanilide, 2-amino-4-(3-chlorophenylsulphonyl)-propionanilide, 2-amino-4-(3-chloro-phenylsulphonyl)-butyranilide, 2-amino-4-(3-chloro-phenylsulphonyl)-acetanilide, 2-amino-4-(2-chloro-phenylsulphonyl)-propionanilide, 2-amino-4-(2-chloro-phenylsulphonyl)-butyranilide, 2-amino-4-(2-chloro-phenylsulphonyl)-acetanilide, 2-amino-4-(4-methoxy-phenylsulphonyl)-propionanilide, 2-amino-4-(4-methoxy-phenylsulphonyl)-butyranilide, 2-amino-4-(4-methoxyphenylsulphonyl)-acetanilide, 2-amino-4-(3-methoxy-phenylsulphonyl)-propionanilide, 2-amino-4-(3-methoxy-phenylsulphonyl)-butyranilide, 2-amino-4-(3-methoxy-phenylsulphonyl)-acetanilide, 2-amino-4-( 4-methylthio-phenylsulphonyl)-propionanilide, 2-amino-4-(4-methylthio-phenylsulphonyl)-butyranilide, 2-amino-4-(4-methylthio-phenylsulphonyl)-acetanilide, 2-amino-4-(3-methylthio-phenylsulphonyl)-propionanilide, 2-amino-4-(3-methylthio-phenylsulphonyl)-butyranilide, 2-amino-4-(3-methylthio-phenylsulphonyl)-acetanilide, 2-amino-4-(4-cyano-phenylsulphonyl)-propionanilide, 2-amino-4-(4-cyano-phenylsulphonyl)-butyranilide, 2-amino-4-(4-cyano-phenylsulphonyl)-acetanilide, 2-amino-4-(3-cyano-phenylsulphonyl)-propionanilide, 2-amino-4-(3-cyano-phenylsulphonyl)-butyranilide, 2-amino-4-(3-cyano-phenylsulphonyl)-acetanilide, 2-amino-4-(4-acetyl-phenylsulphonyl)-propionanilide, 2-amino-4-(4-acetylphenylsulphonyl)-butyranilide, 2-amino-4-(4-acetyl-phenylsulphonyl)-acetanilide, 2-amino-4-(4-propionyl-phenylsulphonyl)-propionanilide, 2-amino-4-(4-propionyl-phenylsulphonyl)-butyranilide, 2-amino-4-(4-propionayl-phenylsulphonyl)-acetanilide, 2-amino-4-(4-acetylamino-phenylsulphonyl)-propionanilide, 2-amino-4-(4-acetylamino-phenylsulphonyl)-butyranilide, 2-amino-4-(4-acetylamino-phenylsulphonyl)-acetanilide, 2-amino-4-(4-methoxycarbonylamino-phenylsulphonyl)-propionanilide, 2-amino-4-(4-methoxycarbonylamino-phenylsulphonyl)-butyranilide, 2-amino-4-(4-methoxycarbonylamino-phenylsulphonyl)-acetanilide, 2-amino-4-(4-methoxycarbonyl-phenylsulphonyl)-propionanilide, 2-amino-4-(4-methoxycarbonyl-phenylsulphonyl)-butyranilide, 2-amino-4-(4-methoxycarbonyl-phenylsulphonyl)-acetanilide, 2-amino-4-(3,4-dimethyl-phenylsulphonyl)-propionanilide, 2-amino-4-(3,4-dimethyl-phenylsulphonyl)-butyranilide, 2-amino-4-(3,4-dimethyl-phenylsulphonyl)-acetanilide, 2-amino-4-(2-methyl-4-chloro-phenylsulphonyl)-propionanilide, 2-amino-4-(2-methyl-4-chloro-phenylsulphonyl)-acetanilide, 2-amino-4-(4-ethyl-phenylsulphonyl)-propionanilide, 2-amino-4-(4-ethyl-phenylsulphonyl)-butyranilide, 2-amino-4-(4-ethyl-phenylsulphonyl)-acetanilide, 2-amino-4-(3,4-dichloro-phenylsulphonyl)-propionanilide, 2-amino-4-(3,4-dichloro-phenylsulphonyl)-butyranilide, 2-amino-4-(3,4-dichloro-phenylsulphonyl)-acetanilide, 2-amino-4-(4-bromo-phenylsulphonyl)-propionanilide, 2-amino-4-(4-bromo-phenylsulphonyl)-butyranilide, 2-amino-4-(4-bromo-phenylsulphonyl)-acetanilide, 2-amino-4-(3,5-dimethylphenylsulphonyl)-propionanilide, 2-amino-4-(3,5-dimethylphenylsulphonyl)-butyranilide, 2-amino-4-(3,5-dimethyl-phenylsulphonyl)-acetanilide, 2-amino-4-(4-butyl-phenylsulphonyl)-propionanilide, 2-amino-4-(4-butyl-phenylsulphonyl)-butyranilide, 2-amino-4-(4-butyl-phenylsulphonyl)-acetanilide, 2-amino-4-(3-butyl-phenylsulphonyl)-propionanilide, 2-amino-4-(3-butyl-phenylsulphonyl)-butyranilide and 2-amino-4-(3-butyl-phenylsulphonyl)-acetanilide.

The following may be mentioned individually as new active compounds: N-(2-acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-ethoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidine, N-(2-propionamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-butyramido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-valeramido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclopentanecarboxylic acid amino-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-benzamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-cyclohexanecarbonyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidine, N-[2-(2'-methylureido)-4-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ethylureiod)-4-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2(2'-butylureido)-4-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-4-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-β-methoxymethylureido)-4-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-benzylureido)-4-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-phenylureido)-4-phenoxy-phenyl]-N'-methoxycarbonyl-N"propionyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N',N"-bis-ethoxycarbonyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N',N"-bis-sec.-butoxycarbonyl-guanidine, N-(2-propionamido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-butyramido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-butyramido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-valeramido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-valeramido-4-phenoxyphenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-caproamido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-caproamido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-4-phenoxyphenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenylacetamido-4-phenoxy-phenyl)-N' ,N"-bis-methoxycarbonyl-guanidine, N-(2-phenoxyacetamido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-benzamido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-methylureido)-4-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ethylureido)-4-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-butylureido)-4-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-4-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-β-methoxyethyl-ureido)-4-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-benzylureido)-4-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-phenylureido)-4-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-]2-propionamido-4-(3-methyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-chloro-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-chlorophenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(2-chloro-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methoxy-phenoxy)phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methoxy-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methylthio-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamide-4-(3-methylthio-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-cyano-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-acetylphenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido- 4-(3-cyano-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-propionyl-phenoxy)phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-acetylamino-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methoxycarbonylphenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3,4-dimethyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3,4-dichlorophenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N'-ethoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidine, N-(2-propionamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-butyramido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-valeramido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-5-phenoxy-phenyl)-N'-methoxy-carbonyl-N"-propionyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-benzamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-cyclohexanecarbonyl-guanidine, N-(2-acetamido-5-phenoxyphenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidine, N-[2-(2'-methylureido)-5-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ethylureido)-5-phenoxy-phenyl]-N'-methoxycarbonyl-N"- propionyl-guanidine, N-[2-(2'-butylureiod)-5-phenoxy-phenyl] -N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ω -cyanopentylureido)-5-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-β-methoxymethylureido)-5-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-benzylureido)-5-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-phenylureido)-5-phenoxy-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N',N"-bis-ethoxycarbonyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine, N-(2-acetamido-5-phenoxy-phenyl)-N',N"-bis-sec.-butoxycarbonyl-guanidine, N-(2-propionamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-butyramido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-butyramido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-valeramido-5phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-valeramido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2caproamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-caproamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenylacetamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenoxy-acetamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-benzamido-5-phenoxy-phenyl)-N',N"-bis-methoxy-carbonyl-guanidine, N-[2-(2'-methylureido)-5-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ethylureido)-5-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-butylureido)-5-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ω-cyanopentylureido)- 5-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-β-methoxyethylureido)-5-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-benzylureido)-5-phenoxy-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-phenylureido)-5-phenoxy-phenyl] -N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methyl-phenoxy)-phenyl]-N',N"-bismethoxycarbonyl-guanidine, N-[2-propionamido-5-(4-chlorophenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-chloro-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(2-chloro-phenoxy)phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methoxy-phenoxy)-phenyl]-N',N"-bis-methoxycarbonylguanidine, N-[2-propionamido-5-(4-methylthio-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methylthio-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-cyano-phenoxy)-phenyl]-N',N"-bismethoxycarbonyl-guanidine, N-[2-propionamido-5-(4-acetyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-cyano-phenoxy)-phenyl]-N',N"-bis-methoxycarbonylguanidine, N-[2-propionamido-5-(4-propionyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-acetylamino-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methoxycarbonyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3,4-dimethyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3,4-dichloro-phenoxy)-phenyl]-N',N"-bismethoxycarbonyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N' -ethoxycarbonyl-"-propionyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidine, N-(2-propionamido4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-butyramido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-valeramido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-4-phenylthio-phenyl)-N'methoxycarbonyl-N"-propionyl-guanidine, N-(2-benzamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-cyclohexanecarbonyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidine, N-[2-(2'-methylureido)-4-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ethylureido)-4-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-(2'-butylureido)-4-phenylthiophenyl]-N'-methoxycarbonylN"-propionyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-4-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-β-methoxymethylureido)-4-phenylthio-phenyl] -N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-benzylureido)-4-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-phenylureido)-4-phenylthiophenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N',N"-bis-ethoxycarbonyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N',N"-bis-sec.-butoxycarbonyl-guanidine, N-(2-propionamido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonylguanidine, N-(2-butyramido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-butyramido-4-phenylthiophenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-valeramido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine,N-(2-iso-valeramido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-caproamido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine,N-(2-iso-caproamido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-4-phenylthio-phenyl)-N',N"-bismethoxycarbonyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenylacetamido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenoxyacetamido-4-phenylthiophenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-benzamido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-methylureido)-4-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ethylureido)-4-phenylthiophenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2(2'-butylureido)-4-phenylthio-phenyl]-N',N"-bis-methoxy-carbonylguanidine, N-[2-(2'ω-cyanopentylureido)-4-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'β-methoxyethylureido)-4-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-benzylureido)-4-phenylthio-phenyl]-N',N"-bismethoxycarbonyl-guanidine, N-2-(2'-phenylureido)-4-phenylthio-phenyl]N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-chloro-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-chloro-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(2-chloro-phenylthio)-phenyl]N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methoxy-phenylthio)phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methoxy-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methylthio-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methylthio-phenylthio)-phenyl]-N',N" bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-cyanophenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-acetyl-phenylthio)-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-cyano-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-propionyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-acetylaminophenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methoxycarbonyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3,4-dimethyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3,4-dichloro-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N'-ethoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylthio-phenyl)-N'-isopropoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidine, N-(2-propionamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-butyramido-5-phenylthiophenyl)-N'-methoxycarbonyl-N" -propionyl-guanidine, N-(2-valeramido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-5-amido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-benzamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N-"-cyclohexanecarbonylguanidine, N-(2-acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidine, N-(2-acetamido-5-phenylthiophenyl)-N"-methoxycarbonyl-N"-phenylacetyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidine, N-[2-(2'-methylureido)-5-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ethylureido)-5-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-butylureido)-5-phenylthiophenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-5-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-β-methoxymethylureido)-5-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-benzylureido)-5-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-phenylureido)-5-phenylthio-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonylguanidine, N-(2-acetamido-5-phenylthio-phenyl)-N',N"-bisethoxycarbonyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine, N-(2-acetamido-5-phenylthio-phenyl)-N' ,N"-bis-sec.-butoxycarbonyl-guanidine, N-(2-propionamido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-butyramido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-butyramido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-valer amido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-valeramido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-caproamido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-caproamido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenylacetamido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenoxyacetamido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-benzamido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-methylureido)-5-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ethylureido)-5-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-butylureido)-5-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-5-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-β-methoxyethylureido)-5-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-benzylureido)-5-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-phenylureido)-5-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2 -propionamido-5-(4-methyl-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-chloro-phenylthio)-phenyl] -N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3 -chloro-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-chloro-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methoxy-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methoxy-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methylthio-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methylthio-phenylthio-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[-methylthio-phenylthio)-phenyl]-propionamido-5-(4-cyano-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-acetyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-cyano-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-propionyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-acetylamino-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methoxycarbonyl-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3,4-dimethylphenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3,4-dichloro-phenylthio)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-ethoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidine, N-(2-propionamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-butyramido-4-phenylsulphinyl-phenyl)-n'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-valeramido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-4-phenylsulphinyl-phenyl)-N' -methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-benzamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-cyclohexanecarbonyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidine, N-[2-(2'-methylureido)-4-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ethylureido)-4-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-butylureido)-4-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-4-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-β-methoxymethylureido)-4-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-benzylureido)-4-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-phenylureido)-4-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine, N-(2-acetamido-4-phenylsulphinyl-phenyl)-N',N"-bis-sec.-butoxycarbonyl-guanidine, N-(2-propionamido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-butyramido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-butyramido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-valeramido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-valeramido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-caproamido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-caproamido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenylacetamido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenoxyacetamido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-benzamido-4-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-methylureido)-4-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ethylureido)-4-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-butylureido)-4-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-4-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-β-methoxyethyl-ureido)-4-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-benzylureido)-4-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-phenylureido)-4-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2 -propionamido-4-(4-methyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-chloro-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido- 4-(3-chloro-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(2-chloro-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methoxy-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methoxy-phenylsulphinyl)-phenyl]-N'-(-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methylthio-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methylthio-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-cyano-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-acetyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-cyano-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-propionyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-acetylamino-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methoxycarbonyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3,4-dimethyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4(3,4-dichloro-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-ethoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidine, N-(2-propionamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-butyramido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-( 2-valeramido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-benzamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-cyclohexanecarbonyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidine, N-[2-(2'-methylureido)-5-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ethylureido)-5-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-butylureido)-5-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-5-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propinyl-guanidine, N-[2-(2'-β-methoxymethylureido)-5-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-benzyluriedo)-5-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-phenylureido)-5-phenylsulphinyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N',N"-bis-ethoxycarbonyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine, N-(2-acetamido-5-phenylsulphinyl-phenyl)-N',N"-bis-sec.-butoxycarbonyl-guanidine, N-(2 -propionamido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-butyramido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-butyramido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-valeramido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-valeramido-5-phenylsulphinyl-phenyl)-N(,N"-bis-methoxycarbonyl-guanidine, N-(2-caproamido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-caproamido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenylacetamido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenoxyacetamido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-benzamido-5-phenylsulphinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-methylureido)-5-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ethylureido)-5-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-butylureido)-5-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-5-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-β-methoxyethylureido)-5-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-benzylureido)-5-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-phenylreido)-5-phenylsulphinyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propoionamido-5-(4-methyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methylphenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-chloro-phenylsulphinyl)-phenyl] -N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-chlorophenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-chloro-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methoxyphenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methoxy-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methylthio-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methylthio-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-cyano-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-acetyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-cyano-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-propionyl-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-acetylamino-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methoxycarbonyl-phenysulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3,4-dimethyl-phenylsulphinyl)phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3,4-dichloro-phenylsulphinyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-ethoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4 -phenylsulphonyl-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidine, N-(2-propionamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-butyramido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-valeramido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-benzamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-cyclohexanecarbonyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidine, N-[2-(2'-methylureido)-4-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ethylureido)-4-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-butylureido)-4-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-4-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2 -(2'-β-methoxymethylureido)-4-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-benzylureido)-4-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-phenylureido)-4-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidien, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N',N"-bis-ethoxycarbonyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N',N"-bis-sec.-butoxycarbonyl-guanidine, N-(2-propionamido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-butyramido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-butyramido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-valeramido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-valeramido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-caproamido-4-phenylsulphonyl-phenyl-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-caproamido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenylacetamido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenoxyacetamido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-benzamido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-methylureido)-4-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ethylureido)-4-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-butylureido)-4-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-4-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-β-methoxyethyl-ureido)-4-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-benzylureido)-4-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-phenylureido)-4-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methylphenylsulphonyl)-phenyl]-N',N" -bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-chloro-phenylsulphoyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-chloro-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(2-chloro-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methoxy-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methoxy-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methylthio-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-methylthio-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-cyano-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-acetyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3-cyano-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-propionyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-acetylamino-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(4-methoxycarbonyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3,4-dimethyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-4-(3,4-dichloro-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-ethoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-4-phenylsulphonyl-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guandine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N'-sec.-butoxycarbonyl-N"-propionylguanidine, N-(2-propionamido-4-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N" -propionyl-guanidine, N-(2-butyramido- 5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-valeramido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-benzamido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-cyclohexanecarbonyl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidine, N-[2-(2'-methylureido)-5-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ethylureido)-5-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-butylureido)-5-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-5-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-β-methoxymethylureido)-5-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-benzylureido)-5-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-[2-(2'-phenylureido)-5-phenylsulphonyl-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine, N-"-acetamido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N',N"-bis-ethoxycarbonyl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl)-N',N" -bis-isopropoxycarbonyl-guanidine, N-(2-acetamido-5-phenylsulphonyl-phenyl-N',N"-bis-sec.-butoxycarbonyl-guanidine, N-(2-propionamido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-butyramido-5-phenylslphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-butyramido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-valeramido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-valeramido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-caproamido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-iso-caproamido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclopentanecarboxylic acid amido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-cyclohexanecarboxylic acid amido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenylacetamido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-phenoxyacetamido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-(2-benzamido-5-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-methylureido)-5-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ethylureido)-5-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-butylureido)-5-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-ω-cyanopentylureido)-5-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-β-methoxyethyl-ureido)-5-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-benzylureido)-5-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-(2'-phenylureido)-5-phenylsulphonyl-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4 -methyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4 -chloro-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5 -(3-chloro-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-chloro-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methoxy-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methoxy-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methylthio-phenylsulphonyl)phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3-methylthio-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-( 4-cyano-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-acetyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guandine, N-[2-propionamido-5-(3-cyano-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-propionyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4 -acetylamino-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(4-methoxycarbonyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine, N-[2-propionamido-5-(3,4-dimethyl-phenylsulphonyl)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine and N-(2-propionamido-5-(3,4-dichloro-phenylsulphonyl)-phenyl]-N',N"-methoxycarbonyl-guanidine.

The compounds prepared in accordance with the invention show a surprisingly improved action against one or more of the following nematodes and cestodes:

1. Hookworms (for example Uncinaria stenocephala, Ancylostoma caninum and Bunostomum trigonocephalum).

2. Trichostrongylidae (for example Nippostrongylus muris, Haemonchus contortus, Trichostrongylus colubriformis and Ostertagia circumcincta).

3. Strongylidae (for example Oesophagostomum columbianum).

4. Rhabditidae (for example Strongyloides ratti).

5. Ascaridae (for example Ascaris suum, Toxocara canis and Toxascaris leonina).

6. Threadworms (for example Aspiculuris tetraptera).

7. Heterakidae (for example Heterakis spumosa).

8. Whipworms (for example Trichuris muris).

9. Filariae (for example Litomosoides carinii and Dipetalonema witei).

10. Cestodes (for example Hymenolepis nana, Taenia pisiformis and Echinococcus multilocularis).

The action of the compounds of the invention can be conveniently observed in vivo by oral and patenteral administration to test animals heavily infested with parasites.

Hookworm test / sheep and dogs

Sheep experimentally infected with Bunostomum trigonocephalum were treated after the end of the prepatency period of the parasites. The amount of active compound was administered orally as pure active compound in gelatin capsules.

Dogs experimentally infected with Uncinaria stenocephala were treated after the end of the pre-patency period of the parasites. The amount of active compound was administered orally as pure active compound in gelatin capsules.

The effectiveness is determined by counting the worms expelled after the treatment and, after dissection, the worms surviving in the test animals, and calculating the percentage of worms expelled.

The active compounds tested, the dosages used and the action can be seen from the table which follows, which lists the active compounds and the minimum dosage, in mg of active compound per kg of body weight of the test animal, which reduces the worm infection of the test animal by more than 90%.

                                  Table 1__________________________________________________________________________                          Minimum effective doseCompound                       (Red. > 90%) in mg/kg__________________________________________________________________________A1   ##STR4##                    Bunostomum trig. 2.5A2   ##STR5##                    Bunostomum trig. 1A3   ##STR6##                    Uncinaria sten. 5  Bunostomum trig. 1A4   ##STR7##                    Bunostomum trig. 2.5__________________________________________________________________________
Nippostrongylus muris--rats

Rats experimentally infected with Nippostrongylus muris were treated after the end of the pre-patency period of the parasites. The amount of active compound was administered orally as an aqueous suspension.

The effectiveness of the preparation is determined by counting, after dissection, the worms which have remained in the test animal, in comparison to untreated control animals, and calculating the percentage action therefrom.

Table 2 lists the active compounds and the minimum dosage which reduces the worm infection of the test animals by more than 90%, in comparison to related preparations.

                                  Table 2__________________________________________________________________________                          Minimum effective doseCompound                       (Red. > 90%) in mg/kg__________________________________________________________________________B1   ##STR8##                    25B2   ##STR9##                    25B3   ##STR10##                   50B4   ##STR11##                   100Related preparations for comparison (known from DOS(German Published Specification) 2,117,293): ##STR12##                     > 500 ##STR13##                     500__________________________________________________________________________
Stomach and intestine worm test / sheep

Sheep experimentally infected with Haemonchus contortus or Trichostrongylus colubriformis were treated after the end of the pre-patency period of the parasites. The amount of active compound was administered orally as pure active compound in gelatine capsules.

The effectiveness is determined by quantitatively counting the worm eggs, excreted with the faeces, before and after the treatment.

Complete cessation of the excretion of eggs after the treatment denotes that the worms have been expelled or have been so damaged that they can no longer produce any eggs (effective dose).

The active compounds tested and the effective dosages (minimum effective dose) can be seen from Table 3.

                                  Table 3__________________________________________________________________________                                    Minimum effective doseCompound                                 (Red. > 90%) in__________________________________________________________________________                                    mg/kgC1##STR14##                           Haemonchus cont. 5                                    Trichostrong. col. 5C2##STR15##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C3##STR16##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C4##STR17##                           Haemonchus cont. 5                                    Trichostrong. col. 5C5##STR18##                           Haemonchus cont. 5                                    Trichostrong. col. 10C6##STR19##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C7##STR20##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C8##STR21##                           Haemonchus cont. 1                                    Trichostrong. col. 1C9##STR22##                           Haemonchus cont. 2.5                                    Trichostrong. col. 5C10##STR23##                           Haemonchus cont. 5C11##STR24##                           Haemonchus cont. 5                                    Trichostrong. col. 1C12##STR25##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C13##STR26##                           Trichostrong. col. 5  Haemonchus                                    cont. 10C14##STR27##                           Haemonchus cont. 0.5                                    Trichostrong. col. 1C15##STR28##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C16##STR29##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C17##STR30##                           Haemonchus cont. 1                                    Trichostrong. col. 2.5C18##STR31##                           Trichostrong. col. 5C19##STR32##                           Haemonchus cont. 2.5C20##STR33##                           Haemonchus 2.5C21##STR34##                           Trichostrong. col. 5C22##STR35##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C23##STR36##                           Haemonchus cont. 1C24##STR37##                           Haemonchus cont. 1C25##STR38##                           Haemonchus cont. 2.5C26##STR39##                           Haemonchus cont. 2.5                                    Trichostrong. col. 2.5C27##STR40##                           Haemonchus cont. 1                                    Trichostrong. col. 1C28##STR41##                           Haemonchus cont. 1                                    Trichostrong. col. 1C29##STR42##                           Haemonchus cont. 0.5                                    Trichostrong. col. 1C30##STR43##                           Haemonchus cont. 1C31##STR44##                           Haemonchus cont. 5C32##STR45##                           Haemonchus cont. 5C33##STR46##                           Haemonchus cont. 2.5C34##STR47##                           Haemonchus cont. 2.5         Related preparations for comparison (known from DOS         (German Published Specification) 2,117,293) ##STR48##                               Haemonchus cont. >100                                    Trichostrong. col. 50 ##STR49##__________________________________________________________________________                                    Haemonchus cont. 50                                    Trichostrong. col. 10
Ascarid test / dogs and rats

Dogs naturally or experimentally infected with Toxascaris leonina were given the amount of active compound administered orally as pure active compound in gelatine capsules.

The effectiveness is determined by counting the worms expelled after the treatment and, after dissection, the worms surviving in the animals, are calculated in percentage of worms expelled.

Rats experimentally infected with Ascaris suum were treated 2 to 4 days after infection. The amount of active compound was administered orally as an aqueous suspension.

The effectiveness of the preparation is determined by counting, after dissection, the worms which have remained in the test animal in comparison to untreated control animals and calculating the percentage action therefrom.

Table 4 lists the active compounds and the minimum dosage which reduces the worm infection of the test animals by more than 90%, in comparison to related preparations.

                                  Table 4__________________________________________________________________________                           Minimum effective doseCompound                        (Red. 90%) in mg/kg__________________________________________________________________________D1    ##STR50##                   Toxascaris leonina                                    25D2    ##STR51##                   Ascaris suum- Larv.                                    25D3    ##STR52##                   Ascaris suum- Larv.                                    25D4    ##STR53##                   Ascaris suum- Larv.                                    100D5    ##STR54##                   Toxascaris Ascaris suum Larv.                                      5 25D6    ##STR55##                   Ascaris suum Larv.                                    50D7    ##STR56##                   Ascaris suum Larv.                                    50D8    ##STR57##                   Ascaris suum Larv.                                    50Related preparation for comparison (known from DOS (GermanPublished Specification) 2,117,293)                           Minimum effective dose                           (Red. > 90%) in mg/kg ##STR58##                      inactive ##STR59##                      inactive__________________________________________________________________________
Aspiculuris tetraptera / mice

Mice naturally infected with Aspiculuris tetraptera were treated after the end of the pre-patency period of the parasites.

The amount of active compound was administered orally as an aqueous suspension.

The effectiveness of the preparation is determined by counting, after dissection, the worms which have remained in the test animal, in comparison to untreated control animals, and calculating the percentage action therefrom. The results are shown in Table 5.

                                  Table 5__________________________________________________________________________                         Minimum effective doseCompound                      (Red.  90%) in mg/kg__________________________________________________________________________E1    ##STR60##                 50E2    ##STR61##                 25E3    ##STR62##                 25E4    ##STR63##                 50Known preparation for comparison (known from DOS(German Published Specification) 2,117,293                         Minimum effective dose                         (Red. >90%)in mg/kg ##STR64##                    inactive__________________________________________________________________________
Hymenolepis nana/mice

Test animals experimentally infected with H.nana are treated after the end of the pre-patency of the parasites. The amount of active compound is administered orally as an aqueous suspension.

The effectiveness of the preparation is determined by counting, after dissection, the worms which have remained in the test animal in comparison to untreated control animals and calculating the percentage action therefrom. The results are shown in Table 6.

                                  Table 6__________________________________________________________________________                          Minimum effective doseCompound                       (Red. > 90%) in mg/kg__________________________________________________________________________F1    ##STR65##                  500F2    ##STR66##                  500__________________________________________________________________________

The compounds of the invention are employed to combat helmintic infestations, both prophylactically and therapeutically, in humans and other animals through administration thereto of an anthelmintically effective amount of one or more compounds. Generally such an amount will range from about 0.1 mg/kg to about 50 mg/kg of body weight, depending upon the stage and severity of the infestation. This range is of course merely a guideline and the actual dose should be titrated to the recipient keeping in mind his age, general health and body weight, the response to treatment and the type of formulation. At times less than 0.1 mg/kg will suffice while at others more than 50 mg/kg can be indicated. The total daily dose thus will generally be from about 5 mg to about 5 g, although here again this is merely a guideline.

The compounds of the present invention are administered parenterally or orally in any of the usual pharmaceutical forms. These include solid and liquid oral unit dosage forms such as tablets, capsules, powders, suspensions, solutions, syrups and the like, including sustained release preparations, and fluid injectable forms such as sterile solutions and suspensions. The term unit dosage form as used in this specification and the claims refer to physically discrete units to be administered in single or multiple dosage to animals, each unit containing a predetermined quantity of active material in association with the required diluent, carrier or vehicle. The quantity of active material is that calculated to produce the desired therapeutic effect upon administration of one or more of such units.

Powders are prepared by comminuting the compound to a suitable fine size and mixing with a similarly comminuted diluent pharmaceutical carrier such as an edible carbohydrate material as for example, starch. Sweetening, flavoring, preservative, dispersing and coloring agents can also be present.

Capsules are made by preparing a powder mixture as described above and filling formed gelatin sheaths. A lubricant such as talc, magnesium stearate and calcium stearate can be added to the powder mixture as an adjuvant before the filling operation; a glidant such as colloidal silica may be added to improve flow properties; a disintegrating or solubilizing agent may be added to improve the availability of the medicament when the capsule is ingested.

Tablets are made by preparing a powder mixture, granulating or slugging, adding a lubricant and disintegrant and pressing into tablets. A powder mixture is prepared by mixing the compound, suitably comminuted, with a diluent or base such as starch, sucrose, kaolin, dicalcium phosphate and the like. The powder mixture can be granulated by wetting with a binder such as syrup, starch paste, acacia mucilage or solutions of cellulosic or polymeric materials and forcing through a screen. As an alternative to granulating, the powder mixture can be run through the tablet machine and the resulting imperfectly formed slugs broken into granules. The granules can be lubricated to prevent sticking to the tablet forming dies by means of the addition of stearic acid, a stearate salt, talc or mineral oil. The lubricated mixture is then compressed into tablets. The medicaments can also be combined with free flowing inert carriers and compressed into tablets directly without going through the granulating or slugging steps. A protective coating consisting of a sealing coat of shellac, a coating of sugar or polymeric material and a polish coating of wax can be provided. Dyestuffs can be added to these coatings to distinguish different unit dosages.

Oral fluids such as syrups and elixirs can be prepared in unit dosage form so that a given quantity, e.g., a teaspoonful, contains a predetermined amount of the compound. Syrups can be prepared by dissolving the compound in a suitably flavored aqueous sucrose solution while elixirs are prepared through the use of a non-toxic alcoholic vehicle. Suspensions can be formulated by dispersing the compound in a non-toxic vehicle in which it is insoluble.

Fluid unit dosage forms for parenteral administration can be prepared by suspending or dissolving a measured amount of the compound in a non-toxic liquid vehicle suitable for injection such as an aqueous or oleaginous medium and sterilizing the suspension or solution. Alternatively a measured amount of the compound is placed in a vial and the vial and its contents are sterilized and sealed. An accompanying vial or vehicle can be provided for mixing prior to administration.

The following examples will serve to further illustrate the compound of the invention and the methods of preparation without being a limitation on the scope thereof, the scope being defined solely by the appended claims.

EXAMPLE 1 ##SPC4##

24.2 g (0.1 mol) of 2-amino-5-phenoxy-acetanilide of melting point 120 C together with 20.6 g (0.1 mol) of N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether and 2.6 g (0.015 mol) of p-toluenesulphonic acid in 200 ml of absolute methanol are boiled for 3 hours with stirring under reflux. The mixture is then filtered hot and after cooling the N-(2-acetamido-4-phenoxyphenyl)-N',N"-bis-methoxycarbonyl-guanidine which has crystallized out is filtered off, rinsed with ether and dried in a high vacuum; melting point 168 C, yield 27 g = 67.5% of theory.

Additional product can be obtained from the mother liquor.

The following reactants are allowed to react in a fashion analogous to Example 1 to yield the following products:

2-amino-5-phenoxy-acetanilide and N,N'-bis-ethoxycarbonylisothiourea-S-methyl-ether gave N-(2-acetamido-4-phenoxyphenyl)-N',N"-bis-ethoxycarbonyl-guanidine of melting point 159 C;

2-amino-5-phenoxy-acetanilide and N,N'-bis-iso-propoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-acetamido-4-phenoxyphenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine of melting point 165 C;

2-amino-5-phenoxy-propionanilide of melting point 122 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-propionamido-4-phenoxyphenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 143 C;

2-amino-5-phenoxy-propionanilide and N,N'-bis-ethoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-propionamido-4-phenoxyphenyl)-N',N"-bis-ethoxycarbonyl-guanidine of melting point 167 C;

2-amino-5-phenoxy-propionanilide and N,N'-bis-isopropoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-propionamido-4-phenoxy-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine of melting point 161 C;

2-amino-5-phenoxy-butyranilide of melting point 118 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-butyramido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 136 C;

2-amino-5-phenoxy-butyranilide and N,N'-bis-ethoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-butyramido-4-phenoxyphenyl)-N',N"-bis-ethoxycarbonyl-guanidine of melting point 142 C;

2-amino-5-phenoxy-butyranilide and N,N'-bis-isopropoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-butyramido-4-phenoxyphenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine of melting point 163 C;

2-amino-5-phenoxy-benzanilide of melting point 140 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-benzamido-4-phenoxyphenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 157 C;

2-amino-5-phenoxy-benzanilide and N,N'-bis-ethoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-benzamido-4-phenoxyphenyl)-N',N"-bis-ethoxycarbonyl-guanidine of melting point 141 C;

2-amino-5-phenoxy-benzanilide and N,N'-bis-iso-propoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-benzamido-4-phenoxyphenyl)-N',N"-bis-iso-propoxycarbonyl-guanidine of melting point 188 C;

2-amino-5-phenoxy-cyclohexanecarboxylic acid anilide of melting point 142 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-cyclohexanecarbonamido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 155 C;

2-amino-5-phenoxy-cyclohexanecarboxylic acid anilide and N,N'-bis-ethoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-cyclohexanecarbonamido-4-phenoxy-phenyl)-N',N"-bis-ethoxycarbonyl-guanidine of melting point 132 C;

2-amino-5-phenoxy-methoxyacetanilide of melting point 93 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-(2-methoxyacetamido-4-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 145 C;

2-amino-5-(3-chloro-phenoxy)-acetanilide and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-acetamido-4-(3-chloro-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 160-161 C;

2-amino-5-(3-chloro-phenoxy)-butyranilide and N,N'-bis-methoxy-carbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(3-chloro-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 163 C;

2-amino-5-(4-chloro-phenoxy)-acetanilide of melting point 150-151 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-acetamido-4-(4-chlorophenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 170 C;

2-amino-5-(4-chloro-phenoxy)-butyranilide of melting point 101 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(4-chloro-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 201 C;

2-amino-5-(3-fluoro-phenoxy)-butyranilide of melting point 121 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(3-fluoro-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 138 C;

2-amino-5-(3-fluoro-phenoxy)-methoxyacetanilide of melting point 106 C and N,N'-bis-methoxy-carbonyl-isothiourea-S-methyl-ether gave N-[2-methoxyacetamido-4-(3-fluorophenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 148 C;

2-amino-5-(3-methoxy-phenoxy)-acetanilide of melting point 107-108 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-acetamido-4-(3-methoxy-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 164 C;

2-amino-5-(3-methoxy-phenoxy)-propionanilide of melting point 129-130 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-propionamido-4-(3-methoxy-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 133-134 C;

2-amino-5-(4-methyl-phenoxy)-propionanilide of melting point 125 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-propionamido-4-(4-methyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 165-166 C;

2-amino-5-(4-methyl-phenoxy)-butyranilide of melting point 122 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(4-methyl-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 161-162 C;

2-amino-5-(4-acetamino-phenoxy)-propionanilide of melting point 200 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-propionamido-4-(4-acetamido-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 197-199 C;

2-amino-5-(4-acetamino-phenoxy)-butyranilide of melting point 150 C and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(4-acetamido-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine of melting point 190 C;

2-amino-5-(4-cyano-phenoxy)-butyr-anilide and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(4-cyano-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine;

2-amino-5-(4-fluoro-phenoxy)-butyr-anilide and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(4-fluoro-phenoxy)-phenyl]-N',N"-bis-methoxy carbonyl-guanidine;

2-amino-5-(4-acetyl-phenoxy)-butyr-anilide and N,N'-bismethoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(4-acetyl-phenoxy)-phenyl]-N',N"-bismethoxycarbonyl-guanidine;

2-amino-5-(3-acetyl-phenoxy)-butyr-anilide and N,N'-bismethoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(3-acetyl-phenoxy)-phenyl]-N',N"-bismethoxycarbonyl-guanidine;

2-amino-5-(4-methylthio-phenoxy)-butyranilide and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(4methylthio-phenoxy)-phenyl]-N',N"-bis-methoxycarbonyl-guanidine;

2-amino-5-(3-trifluoromethyl-phenoxy)-butyranilide and N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(3-trifluoromethyl-phenoxy)phenyl]-N',N"-bis-methoxycarbonyl-guanidine.

EXAMPLE 2 ##SPC5##

24.2 g (0.1 mol) of 2-amino-5-phenoxy-acetanilide together with 22 g (0.1 mol) of N-methoxycarbonyl-N'-propionylisothiourea-S-methyl-ether and 2.6 g (0.015 mol) of p-toluenesulphonic acid in 200 ml of absolute methanol are boiled for 3 hours with stirring under reflux. The mixture is then filtered hot and after cooling the N-(2-acetamido-4-phenoxyphenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine which has crystallized out is filtered off, well rinsed with ether and dried in a high vacuum; melting point 134 C, yield 20 g = 50% of theory. The yield can be increased by working up the mother liquor.

The following reactants are allowed to react in a fashion analogous to Example 2 to yield the following products:

2-amino-5-phenoxy-propion-anilide and N-methoxycarbonylN'-propionyl-isothiourea-S-methyl-ether gave N-(2-propionamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 132 C;

2-amino-5-phenoxy-butyranilide and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methyl-ether gave N-(2-butyramido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 125 C;

2-amino-5-phenoxy-benzanilide and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methyl-ether gave N-(2-benzamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 151 C;

2-amino-5-phenoxy-cyclohexanecarboxylic acid anilide and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methyl-ether gave N-(2-cyclohexane-carbonamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 139 C;

2-amino-5-phenoxy-acetanilide and N-ethoxycarbonyl-N'-benzoyl-isothiourea-S-methyl-ether gave N-(2-acetamido4-phenoxy-phenyl)-N'-ethoxycarbonyl-N"-benzoyl-guanidine of melting point 179 C;

2-amino-5-phenoxy-butyranilide and N-methoxycarbonyl-N'-cyclohexylcarbonyl-isothiourea-S-methyl-ether gave N-(2-butyramido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N"-cyclohexylcarbonyl-guanidine of melting point 146 C;

2-amino-5-phenoxy-butyranilide and N-methoxycarbonyl-N'-ethoxy-methylcarbonyl-isothiourea-S-methyl-ether gave N-(2-butyramido-4-phenoxy-phenyl)-N'-methoxy-carbonyl-N"-ethoxymethylcarbonyl-guanidine of melting point 137 C;

2-amino-5-(3-chloro-phenoxy)-acetanilide and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methyl-ether gave N-[2-acetamido-4-(3-chloro-phenoxy)-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 163 C;

2-amino-5-(3-chloro-phenoxy)-butyranilide and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(3-chloro-phenoxy)-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 163 C;

2-amino-5-(4-acetamido-phenoxy)-propion-anilide and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methyl-ether gave N-[2-propionamido-4-(4-acetamido-phenoxy)-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 190 C;

2-amino-5-(4-acetamido-phenoxy)-butyranilide and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methylether gave N-[2-butyr-amido-4-(4-acetamido-phenoxy)phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 178-180 C;

2-amino-5-(4-methyl-phenoxy)-butyranilide and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methyl-ether gave N-[2-butyramido-4-(4-methyl-phenoxy)-phenyl]-N'-methoxycarbonyl-N"-propionyl-guanidine of melting point 135 C.

EXAMPLE 3 ##SPC6##

12.8 g (0.05 mol) of 2-amino-4-phenoxy-propionanilide (melting point 110-111 C) in 100 ml of methanol are heated with 10.3 g (0.05 mol) of N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether, with the addition of 1 g of p-toluenesulphonic acid, for 3 hours under reflux. After cooling, the precipitate is filtered off and washed with ether, and after drying 11.1 g of N-(2-propionamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 148-149 C are obtained.

EXAMPLE 4

In a fashion analogous to that described in Example 3, N,N'-bis-methoxycarbonyl-isothiourea-S-methyl ether and N-methoxycarbonyl-N'-propionyl-isothiourea-S-methyl ether are individually reacted with 2-amino-4-phenoxy-acetanilide to yield respectively N-(2-acetamido-5-phenoxyphenyl)-N',N"-bismethoxycarbonyl-guanidine, m.p. 181-182 C and N-(2-acetamido5-phenoxyphenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine m.p. 161-163 C.

By utilizing 2-amino-4-phenoxy-butyranilide with the foregoing isothiourea-S-methyl ethers, there are respectively obtained N-(2-butyramido-5-phenoxyphenyl)-N',N"-bismethoxycarbonyl-guanidine, m.p. 164 C, and N-(2-butyramido-5-phenoxyphenyl)-N'-methoxycarbonyl-N"-propionyl-guanidine, m.p. 155-156 C.

EXAMPLE 5

In a fashion analogous to that described in Example 3, the following compounds are obtained from the corresponding anilide and isothiourea-S-methyl-ether: ##SPC7##

______________________________________R2      R4     R5 R6______________________________________H            propyl      ethyl   ethoxyH            methyl      methyl  ethoxyH            methyl      methyl  methoxyH            methyl      methyl  methoxyH            methyl      methyl  allyloxyH            methyl      methyl  propargyloxyH            methyl      methyl  methoxyH            methyl      methyl  methoxyH            methoxymethyl                    methyl  methoxyH            phenoxymethyl                    methyl  methoxyH            propyl      methyl  butyl4-methyl     propyl      methyl  methoxy3-methyl     propyl      methyl  methoxy2-methyl     propyl      methyl  methoxy4-chloro     propyl      methyl  methoxy3-chloro     propyl      methyl  methoxy4-ethyl      propyl      methyl  methoxy3-methylthio propyl      methyl  methoxy3-methoxy    propyl      methyl  methoxy3-trifluoromethyl        propyl      methyl  methoxy3,5-dimethyl propyl      methyl  methoxy______________________________________
EXAMPLE 6 ##SPC8##

14.3 g (0.05 mol) of 2-amino-5-phenylthio-butyranilide (melting point 152 C) in 100 ml of methanol are heated with 10 g (0.05 mol) of N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether, with addition of 1 g of p-toluenesulphonic acid, for 3 hours. After working up analogously to Example 3, 13.8 g of N-(2-butyramido-4-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 155 C are obtained.

EXAMPLE 7

In a fashion analogous to that of Example 6, the appropriate N,N'-disubstituted isothiourea-S-methyl-ethers and 2-amino-5-phenylthio-anilides are reacted to give the following compounds: ##SPC9##

In this example and in Examples 8, 10, 12, 14, 16 and 18, R3 is hydrogen unless otherwise indicated by the listing of two substituents under R2.

______________________________________R2   R4      R5 R6                                 m.p.(  C)______________________________________H         CH3     CH3                          OCH3                                 160H         CH3     CH3                          C2 H5                                 131-132H         CH3     CH3                          OC2 H5                                 145-146H         C2 H5                  CH3                          OCH3                                 176H         C2 H5                  CH3                          C2 H5                                 130H         C3 H7                  CH3                          OC2 H5                                 128H         C3 H7                  CH3                          C2 H5                                 127H         C4 H9                  CH3                          OCH3                                 137H         C4 H9 iso                  CH3                          OCH3                                 145H         OC2 H5                  CH3                          OCH3                                 159H         C5 H11                  CH3                          OCH3                                 127H         C5 H11                  CH3                          C2 H5                                 122H         C4 H9                  CH3                          C2 H5                                 160      ##STR67##   CH3                          OCH3                                 161H         CH(CH3)2                  CH3                          OCH3                                 161H         CH2 OCH3                  CH3                          OCH.sub. 3                                 129-130H         CH2OC 2 H5                  CH3                          OCH3                                 119H         CH2 OC6 H5                  CH3                          OCH3                                 144-1464-CH3     C3 H7                  CH3                          OCH3                                 1712-Cl      C2 H5                  CH3                          OCH3                                 1444-Br      C3 H7                  CH3                          OCH3                                 1764-C2 H5     C3 H7                  CH3                          OCH3                                 1672,5-(OCH3)2     C3 H7                  CH3                          OCH3                                 1424-CH3     C3 H7                  CH3                          C2 H5                                 1104-Cl      C3 H7                  CH3                          OCH3                                 1764-Cl      C3 H7                  CH3                          C2 H5                                 1552-Cl      C3 H7                  CH3                          OCH3                                 1542-Cl      CH2 OCH3                  CH3                          OCH3                                 1384-Br      C2 H5                  CH3                          OCH3                                 1583-CH3,4-Br     C3 H7                  CH3                          OCH3                                 1703-CH3,4-Br     CH2 OCH3                  CH3                          OCH3                                 1414-C2 H5     C2 H5                  CH3                          OCH3                                 1554-C2 H5     CH2 OCH3                  CH3                          OCH3                                 1263-CF3     CH2 OCH3                  CH3                          OCH3                                 1204-OCH3     CH2 OCH3                  CH3                          OCH3                                 1312-OC2 H9     C3 H7                  CH3                          OCH3                                 1282-OC2 H5     CH2 OCH3                  CH3                          OCH3                                 1102-COOCH3     C3 H7                  CH3                          OCH3                                 1382-COOCH3     C2 H5                  CH3                          OCH3                                 1582-COOCH3     CH2 OCH3                  CH3                          OCH3                                 135H         CH2 OCH3                  CH3                          OC2 H5                                 125-127H         CH2 OC6 H5                  CH3                          C2 H5                                 138-140H         CH2 OC2 H5                  CH3                          C2 H5                                 1114-OCH3     C3 H7                  CH3                          OCH3                                 1853-OCH3     C3 H7                  CH3                          OCH3                                 1604-F       CH2 OCH3                  CH3                          OCH3                                 1274-F       C3 H7                  CH3                          OCH3                                 1554-F       C3 H7                  CH3                          C2 H5                                 136-1374-Br      CH2 OCH3                  CH3                          OCH3                                 1143-Cl      C3 H7                  CH3                          OCH.sub. 3                                 1293-Cl      CH2 OCH3                  CH3                          OCH3                                 1244-C(CH3)3     C3 H7                  CH3                          OCH3                                 169______________________________________
EXAMPLE 8

In a fashion analogous to that described in Example 6, the following compounds are obtained from the corresponding anilide and isothiourea-S-methyl-ether: ##SPC10##

__________________________________________________________________________R2    R4 R5                  R6__________________________________________________________________________H          ethyl   methyl                  ethoxyH          methyl  methyl                  methoxyH          hexyl   methyl                  methoxyH          ethyl   methyl                  allyloxyH          ethyl   methyl                  propargyloxyH          ethyl   methyl                  2-methylprop-2-enyloxyH          ethyl   allyl                  allyloxyH          cyclopentyl              methyl                  methoxyH          cyclohexyl              methyl                  methoxy4-methyl   propyl  methyl                  methoxy3-methyl   propyl  methyl                  methoxy2-methyl   propyl  methyl                  methoxy4-chloro   ethyl   methyl                  methoxy3-chloro   ethyl   methyl                  methoxy4-acetamido      ethyl   methyl                  methoxy3,4-dichloro      propyl  methyl                  methoxy4-butyl    propyl  methyl                  methoxy3-methyl-4-bromo      ethyl   methyl                  methoxy3-trifluoromethyl      propyl  methyl                  methoxy4-butyl    methoxymethyl              methyl                  methoxy3-methoxy  methoxymethyl              methyl                  methoxy2,4-dimethyl      propyl  methyl                  methoxy3-methoxy  propyl  methyl                  methoxy4-methylthio      propyl  methyl                  methoxy2-ethoxy   ethyl   methyl                  methoxy3-methyl-4-bromo      ethyl   methyl                  methoxy3-trifluoromethyl      ethyl   methyl                  methoxy4-acetyl   ethyl   methyl                  methoxy3-acetyl   ethyl   methyl                  methoxy4-butynyl  ethyl   methyl                  methoxy4-carbomethoxyamino      ethyl   methyl                  methoxy4-cyano    ethyl   methyl                  methoxy3-cyano    ethyl   methyl                  metoxy__________________________________________________________________________
EXAMPLE 9 ##SPC11##

Using the method described in Example 3, 14.3 g (0.05 mol) of 2-amino-4-phenylthio-butyranilide and 10.3 g (0.05 mol) of N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether give 14.5 g of N-(2-butyramido-5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 164-166 C.

EXAMPLE 10

In a fashion analogous to that described in Example 9 using the appropriate N,N'-disubstituted isothiourea-S-methyl ethers and 2-amino-4-phenyl-thioanilides, the following compounds are obtained: ##SPC12##

__________________________________________________________________________R2 R4         R5  R6__________________________________________________________________________H       CH3         CH3 OCH3H       CH3         CH3 C2 H5H       CH3         CH3 OC2 H5H       C2 H5         CH3 OCH3H       C2 H5         CH3 C2 H5H       C2 H5         CH3 OC2 H5H       C3 H7         CH3 OC2 H5H       C3 H7         CH3 C2 H5H       C4 H9         CH3 OCH3H       C4 H9 iso         CH3 OCH3H       OCH3         CH3 OCH3H       OC2 H5         CH3 OCH3H       C5 H11         CH3 OCH3H       C6 H13         CH3 OCH3H       C2 H5         CH3 OCH2CHCH 2H       C2 H5         CH3                   ##STR68##H       C2 H5         CH3 OCHC(CH3)CH2H       C2 H.sub. 5         CH2CHCH 2                  OCH2CHCH 2    ##STR69##         CH3 OCH3H    ##STR70##         CH3 OCH3H       CH2 OCH3         CH3 OCH3H       CH2 OC6 H5         CH3 OCH34-CH3   C3 H7         CH3 OCH33-CH3   C3 H7         CH3 OCH32-CH3   C3 H7         CH3 OCH34-Cl    C2 H5         CH3 OCH33-Cl    C2 H5         CH3 OCH32-Cl    C2 H5         CH3 OCH34-NHCOCH3   C2 H5         CH3 OCH34-Br    C3 H7         CH3 OCH33,4-Cl2   C3 H7         CH3 OCH34-C4 H9   C3 H7         CH3 OCH34-C2 H5   C3 H7         CH3 OCH33,5-(CH3)2   C3 H7         CH3 OCH32,4-(CH3)2   C3 H7         CH3 OCH33-OC2 H5   C3 H7         CH3 OCH34-OCH3   C3 H7         CH3 OCH33-OCH3   C3 H7         CH3 OCH34-SCH3   C3 H7         CH3 OCH32-OC2 H5   C2 H5         CH3 OCH33-CH3,   C2 H5         CH3 OCH34-Br3-CF3   C2 H5         CH3 OCH34-F     C2 H5         CH3 OCH34-CH3 CO   C2 H5         CH3 OCH33-CH3 CO   C2 H5         CH3 OCH34-C3 H7 CO   C2 H5         CH3 OCH34-NHCOOCH3   C2 H5         CH3 OCH34-CN    C2 H5         CH3 OCH33-CN    C2 H5         CH3 OCH3__________________________________________________________________________
EXAMPLE 11 ##SPC13##

Using the method described in Example 3, 14.2 g (0.05 mol) of 2-amino-5-phenylsulphinyl-propionanilide and 10.3 g (0.05 mol) of N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether give 12.7 g of N-(2-propionamido-4-phenylsulphinylphenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 193-195 C.

Utilizing 2-amino-5-phenylsulphinylbutyranilide and 2-amino-5-phenylsulphinyl-methoxyacetanilide, there are obtained N-(2-butyramido-4-phenylsulphinylphenyl)-N',N"-bis-methoxycarbonyl-guanidine, m.p. 186 C, and N-(2-methoxyacetamido-4-phenylsulfinylphenyl)-N',N"-bis-methoxycarbonylguanidine, m.p. 135-136 C, respectively.

EXAMPLE 12

In a fashion analogous to Example 11 the corresponding N,N'-disubstituted isothiourea-S-methyl-ethers and 2-amino-5-phenylsulphinylanilides are reacted to yield the following compounds: ##SPC14##

__________________________________________________________________________R2 R4          R5  R6__________________________________________________________________________H       CH3          CH3 OCH3H       CH3          CH3 C2 H5H       CH3          CH3 OC2 H5H       C2 H5          CH3 C2 H5H       C2 H5          CH3 OC2 H5H       C3 H7          CH3 OC2 H5H       C3 H7          CH3 C2 H5H       C4 H9          CH3 OCH3H       C4 H9 iso          CH3 OCH3H       OCH3          CH3 OCH3H       OC2 H5          CH3 OCH3H       C5 H11          CH3 OCH3H       C6 H13          CH3 OCH3H       C2 H5          CH3 OCH2CHCH 2H       C2 H5          CH3                    ##STR71##H       C2 H5          CH3 OCH2C(CH3)CH2H       C2 H5          CHCHCH2                   OCH2CHCH 2    ##STR72##          CH3 OCH3H    ##STR73##          CH3 OCH3H       CH2 OC6 H5          CH3 OCH34-CH3   C3 H7          CH3 OCH33-CH3   C3 H7          CH3 OCH32-CH3   C3 H7          CH3 OCH34-Cl    C2 H5          CH3 OCH33-Cl    C2 H5          CH3 OCH32-Cl    C2 H5          CH3 OCH34-NHCOCH3   C2 H5          CH3 OCH34-Br    C3 H7          CH3 OCH33,4-Cl2   C3 H7          CH3 OCH34-C4 H9   C3 H7          CH3 OCH34-C2 H5   C3 H7          CH3 OCH33,5-(CH3)2   C3 H7          CH3 OCH32,4-(CH3)2   C3 H7          CH3 OCH33-OC2 H5   C3 H7          CH3 OCH34-OCH3   C3 H7          CH3 OCH33-OCH3   C3 H7          CH3 OCH32-OC2 H5   C2 H5          CH3 OCH33-CH3,   C2 H5          CH3 OCH34-Br3-CF3   C2 H5          CH3 OCH34-F     C2 H5          CH3 OCH34-CH3 CO   C2 H5          CH3 OCH33-CH3 CO   C.sub. 2 H5          CH3 OCH34-C3 H7 CO   C2 H5          CH3 OCH34-NHCOOCH3   C2 H5          CH3 OCH34-CN    C2 H5          CH3 OCH33-CN    C2 H5          CH3 OCH3__________________________________________________________________________
EXAMPLE 13 ##SPC15##

Using the method described in Example 3, 14.2 g (0.05 mol) of 2-amino-4-phenylsulphinyl-propionanilide and 10.3 g (0.05 mol) of N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether give 12.7 g of N-(2-propionamido-5-phenylsulphinylphenyl)-N',N"-bis-methoxycarbonyl-guanidine.

EXAMPLE 14

In a fashion analogous to Example 13 the corresponding N,N'-disubstituted isothiourea-S-methyl-ethers and 2-amino-4-phenylsulphinyl-anilides are reacted to yield the following compounds: ##SPC16##

__________________________________________________________________________R       R4          R5  R6__________________________________________________________________________H       CH3          CH3 OCH3H       CH3          CH3 C2 H5H       CH3          CH3 OC2 H5H       C3 H7          CH3 OCH3H       C2 H5          CH3 C2 H5H       C2 H5          CH3 OC2 H5H       C3 H7          CH3 OC2 H5H       C3 H7          CH3 C2 H5H       C4 H9          CH3 OCH3H       C4 H9 iso          CH3 OCH3H       CH3          CH3 OCH3H       OC2 H5          CH3 OCH3H       C5 H11          CH3 OCH3H       C6 H13          CH3 OCH3H       C2 H5          CH3 OCH2CHCH 2H       C2 H5          CH3                    ##STR74##H       C2 H5          CH3 OCH2C(CH3)CH2H       C2 H.sub. 5          CH2CHCH 2                   OCH2CHCH 2    ##STR75##          CH3 OCH3H    ##STR76##          CH3 OCH3H       CH2 OCH3          CH3 OCH3H       CH2 OC6 H5          CH3 OCH34-CH3   C3 H7          CH3 OCH33-CH3   C3 H7          CH3 OCH32-CH3   C3 H7          CH3 OCH34-Cl    C2 H5          CH3 OCH33-Cl    C2 H5          CH3 OCH32-Cl    C2 H5          CH3 OCH34-NHCOCH3   C2 H5          CH3 OCH34-Br    C3 H7          CH3 OCH33,4-Cl2   C3 H7          CH3 OCH34-C4 H9   C3 H7          CH3 OCH34-C2 H5   C3 H7          CH3 OCH33,5-(CH3)2   C3 H7          CH3 OCH32,4-(CH3)2   C3 H7          CH3 OCH33-OC2 H5   C3 H7          CH3 OCH34-OCH3   C.sub. 3 H7          CH3 OCH33-OCH3   C3 H7          CH3 OCH34-SCH3   C3 H7          CH3 OCH32-OC2 H5   C2 H5          CH3 OCH33-CH3,   C2 H5          CH3 OCH34-Br3-CF3   C2 H5          CH3 OCH34-F     C2 H5          CH3 OCH34-CH3 CO   C2 H5          CH3 OCH33-CH3 CO   C2 H5          CH3 OCH34-C3 H7 CO   C2 H5          CH3 OCH34-NHCOOCH3   C2 H5          CH3 OCH34-CN    C2 H5          CH3 OCH33-CN    C2 H5          CH3 OCH3__________________________________________________________________________
EXAMPLE 15 ##SPC17##

Using the method described in Example 3, 14.4 g (0.05 mol) of 2-amino-5-phenylsulphonyl-propionanilide of melting point 137 C and 10.3 g (0.05 mol) of N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether give 12.7 g of N-(2-propionamido-4-phenylsulphonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 197 C.

Substituting 2-amino-5-phenylsulphonylbutyranilide and 2-amino-5-phenylsulphonylmethoxyacetanilide, there are obtained N-(2-butyrylamido-4-phenylsulphonylphenyl)-N',N"-bis-methoxycarbonyl-guanidine, m.p. 180 C, and N-(2-methoxyacetamido-4-phenylsulphonylphenyl)-N',N"-bis-methoxycarbonyl-guanidine, m.p. 142 C.

EXAMPLE 16

In a fashion analogous to Example 15 the corresponding N,N'-disubstituted isothiourea-S-methyl-ethers and 2-amino-5-phenylsulphonylanilides are reacted to yield the following compounds: ##SPC18##

__________________________________________________________________________R2 R4         R5  R6__________________________________________________________________________H       CH3         CH3 OCH3H       CH3         CH3 C2 H5H       CH3         CH3 OC2 H5H       C2 H5         CH3 C2 H5H       C2 H5         CH3 OC2 H5H       C3 H7         CH3 OC2 H5H       C3 H7         CH3 C2 H5H       C4 H9         CH3 OCH3H       C4 H9 iso         CH3 OCH3H       OCH3         CH3 OCH3H       OC2 H5         CH3 OCH3H       C5 H11         CH3 OCH3H       C6 H13         CH3 OCH3H       C2 H5         CH3 OCH2CHCH 2H       C2 H5         CH3                   ##STR77##H       C2 H5         CH3 OCHC(CH3)CH2H       C2 H5         CH2CHCH 2                  OCH2CHCH.sub. 2    ##STR78##         CH3 OCH3H    ##STR79##         CH3 OCH3H       CH2 OC6 H5         CH3 OCH34-CH3   C3 H7         CH3 OCH33-CH3   C3 H7         CH3 OCH32-CH3   C3 H7         CH3 OCH34-Cl    C2 H5         CH3 OCH33-Cl    C2 H5         CH3 OCH32-Cl    C2 H5         CH3 OCH34-NHCOCH3   C2 H5         CH3 OCH34-Br    C3 H7         CH3 OCH33,4-Cl2   C3 H7         CH3 OCH34-C4 H9   C3 H7         CH3 OCH34-C2 H5   C3 H7         CH3 OCH33,5-(CH3)2   C3 H7         CH3 OCH32,4-(CH3)2   C3 H7         CH3 OCH33-OC2 H5   C3 H7         CH3 OCH34-OCH3   C3 H7         CH3 OCH33-OCH3   C3 H7         CH3 OCH32-OC2 H5   C2 H5         CH3 OCH33-CH3,   C2 H5         CH3 OCH34-Br3-CF3   C2 H5         CH3 OCH34-F     C2 H5         CH3 OCH34-CH3 CO   C2 H5         CH3 OCH33-CH3 CO   C2 H5         CH3 OCH34-C3 H7 CO   C2 H5         CH3 OCH34-NHCOOCH3   C2 H5         CH3 OCH34-CN    C2 H5         CH3 OCH33-CN    C2 H5         CH3 OCH3__________________________________________________________________________
EXAMPLE 17 ##SPC19##

14.4 g (0.05 mol) of 2-amino-4-phenylsulphonylbutyranilide (melting point 143-145) in 100 ml of methanol are heated with 10.3 g (0.05 mol) of N,N'-bis-methoxycarbonyl-isothiourea-S-methyl-ether, with addition of 1 g of p-toluenesulphonic acid, for 3 hours. After working up analogously to Example 3, 15.8 g of N-(2-butyramido-5-phenylsulphonylphenyl)-N',N"-bis-methoxycarbonyl-guanidine of melting point 173 C are obtained.

EXAMPLE 18

In a fashion analogous to Example 17, the corresponding N,N'-disubstituted isothiourea-S-methyl-ethers and 2-amino-5-phenylsulphonylanilides are reacted to yield the following compounds: ##SPC20##

__________________________________________________________________________R2 R4          R5  R6__________________________________________________________________________H       CH3          CH3 OCH3H       CH3          CH3 C2 H5H       CH3          CH3 OC2 H5H       C2 H5          CH3 OCH3H       C2 H5          CH3 C2 H5H       C2 H5          CH3 OC2 H5H       C3 H7          CH3 OC2 H5H       C3 H7          CH3 C2 H5H       C4 H9          CH3 OCH3H       C4 H9 iso          CH3 OCH3H       OCH3          CH3 OCH3H       OC2 H5          CH3 OCH.sub. 3H       C5 H11          CH.sub. 3                   OCH3H       C6 H13          CH3 OCH3H       C2 H5          CH3 OCH2CHCH 2H       C2 H5          CH3                    ##STR80##H       C2 H5          CH3 OCH2C(CH3)CH2H       C.sub. 2 H5          CH2CHCH 2                   OCH2CHCH 2    ##STR81##          CH3 OCH3H    ##STR82##          CH3 OCH3H       CH2 OCH3          CH3 OCH3H       CH2 OC6 H5          CH3 OCH34-CH3   C3 H7          CH3 OCH33-CH3   C3 H7          CH3 OCH32-CH3   C3 H7          CH3 OCH34-Cl    C2 H5          CH3 OCH33-Cl    C2 H5          CH3 OCH32-Cl    C2 H5          CH3 OCH34-NHCOCH3   C2 H5          CH3 OCH34-Br    C3 H7          CH3 OCH33,4-Cl2   C3 H7          CH3 OCH34-C4 H9   C3 H7          CH3 OCH34-C2 H5   C3 H7          CH3 OCH33,5-(CH3)2   C3 H7          CH3 OCH32,4-(CH3)2   C3 H7          CH3 OCH33-OC2 H5   C3 H7          CH3 OCH34-OCH3   C3 H7          CH3 OCH33-OCH3   C3 H7          CH3 OCH34-SCH3   C3 H7          CH3 OCH32-OC2 H5   C2 H5          CH3 OCH33-CH3,4-Br   C2 H5          CH3 OCH33-CF3   C2 H5          CH3 OCH34-F     C2 H5          CH3 OCH34-CH3 CO   C2 H5          CH3 OCH33-CH3 CO   C2 H5          CH3 OCH34-C3 H7 CO   C2 H5          CH3 OCH34-NHCOOCH3   C2 H5          OCH3                   OCH34-CN    C2 H5          OCH3                   OCH33-CN    C2 H5          OCH3                   OCH3__________________________________________________________________________
EXAMPLE 19 ##SPC21##

2.3 ml of H2 O2 (30%) are added dropwise to a solution of 8.9 g of N-(2-butyramido-4-phenylthiophenyl)-N',N"-bis-methoxycarbonyl-guanidine (m.p. 155 C, Example 4) in 1.4 1 of acetic acid anhydride. After 10 hours the batch is concentrated in vacuo, a mixture of ethyl acetate and petroleum ether added to the residue and filtered. 8.5 g of N-(2-butyramido-4-phenylsulphinylphenyl)-N,N'-bis-methoxycarbonyl-guanidine are obtained with a m.p. of 186 C (decomp.), (redissolved from methanol/ethyl acetate). The mass spectrum shows a mol peak of 460.

Using the same method, 30 g of N-(2-methoxyacetamido-4-phenylsulphinylphenyl)-N',N"-bis-methoxycarbonyl-guanidine with a m.p. of 134 C are obtained from 31.2 g of N-(2-methoxy acetamido-4-phenylthiophenyl)-N',N"-bis-methoxycarbonyl-guanidine and 8.5 ml of H2 O2 (30%).

EXAMPLE 20 ##SPC22##

According to the method described in Example 19, 12.7 g of N-(2-butyramido-4-phenyl-sulphonyl-phenyl)-N',N"-bis-methoxy carbonyl-guanidine of m.p. 180 C are obtained from 13.3 g of N-(2-butyramido-4-phenylthio-phenyl)-N',N" bis-methoxy carbonyl-guanidine and 20 ml of H2 O2 (30%). The mass spectrum shows a mol peak of 476. In an analogous manner, 8.0 g of N-(2-methoxy acetamido-4-phenylsulphonyl-phenyl)-N', N"-bis-methoxy carbonyl-guanidine with a m.p. of 142 C are obtained from 8.9 g of N-(2-methoxy-acetamido-4-phenylthio-phenyl)-N',N"-bis-methoxy carbonyl-guanidine and 14 g of H2 O2 (30%).

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3828094 *22 Oct 19706 Aug 1974Bayer AgSubstituted ureidophenylguanidines
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4127670 *22 Feb 197728 Nov 1978Bayer Aktiengesellschaft2-Formamido phenylguanidines and processes for their preparation and use
US4217358 *18 Apr 197912 Aug 1980E. R. Squibb & Sons, Inc.Substituted phenylguanidines and method
US4246260 *19 Mar 197920 Jan 1981Bayer AktiengesellschaftSubstituted omicron-phenylenediamine derivatives, process for their preparation and their use as medicaments
US4277467 *10 Sep 19797 Jul 1981Bayer AktiengesellschaftEndoparasiticidal pastes for horses
US4293569 *12 May 19786 Oct 1981E. R. Squibb & Sons, Inc.Substituted phenylguanindines and method
US4328241 *20 Jul 19814 May 1982E. R. Squibb & Sons, Inc.Substituted phenylguanidines and method
US5036069 *12 Oct 198930 Jul 1991Bayer AktiengesellschaftAnthelmintic active compound combinations
US65346397 Jul 200018 Mar 2003Isis Pharmaceuticals, Inc.Guanidinium functionalized oligonucleotides and method/synthesis
US65934667 Jul 199915 Jul 2003Isis Pharmaceuticals, Inc.Guanidinium functionalized nucleotides and precursors thereof
US691414820 Sep 20025 Jul 2005Isis Pharmaceuticals, Inc.Guanidinium functionalized intermediates
US700188921 Jun 200221 Feb 2006Merial LimitedAnthelmintic oral homogeneous veterinary pastes
US73968198 Aug 20038 Jul 2008Virbac CorporationAnthelmintic formulations
US739682012 Mar 20048 Jul 2008Virbac CorporationAnthelmintic formulations
US756377315 Apr 200521 Jul 2009Merial LimitedAnthelmintic oral homogeneous veterinary pastes
US75826123 Aug 20041 Sep 2009Hartz Mountain CorporationMulti-action anthelmintic formulations
US789327118 Jul 200622 Feb 2011Intervet International B.V.Benzimidazole carbamates and (thio) carbamates, and the synthesis and use thereof
WO2001002423A2 *7 Jul 200011 Jan 2001Phillip Dan Cook2'-guanidinyl-substituted oligonucleotides and gene expression modulation therewith